Sulfonamides

ABSTRACT

Sulfonamides of the formula I ##STR1## where A is an unsubstituted or substituted aromatic or heteroaromatic radical; W is oxygen or sulfur; B is an unsubstituted or substituted furyl, thienyl, pyrrolyl, oxazolyl, isothiazolyl, imidazolyl, pyrazolyl, thiadiazolyl, oxadiazolyl or triazolyl radical, and the environmentally compatible salts thereof are prepared as described and are used as herbicides.

The present invention relates to sulfonamides of the formula I ##STR2## where A is ##STR3## W is oxygen or sulfur; B is 2-, 3-, 4- or 5-furyl, 2-, 3-, 4- or 5-thienyl, each trisubstituted by R⁸ ; 2-, 3-, 4- or 5-pyrrol which is trisubstituted on carbon by R⁸ and monosubstituted on nitrogen by R⁹ ; 2-, 4- or 5-oxazolyl, 3-, 4- or 5-isoxazolyl 2-, 4- or 5-thiazolyl or 3-, 4- or 5-isothiazolyl, each disubstituted by R⁸ ; 2-, 4- or 5-imidazolyl or 3-, 4- or 5-pyrazolyl, each disubstituted on carbon by R⁸ and monosubstituted on nitrogen by R⁹ ; 1,3,4-thiadiazol-2-yl,-5-y1,1,3,4-oxadiazol-2-yl,-5-yl, 2,4-thiadiazol-3-yl,-5-yl, 1,2,4-oxadiazol-3-yl,-5-yl, 1,2,3-thiadiazol-4-yl,-5-yl, 1,2,3-oxadiazol-4-yl,-5-yl, 1,2,5-thiadiazol-3-yl,-4-yl, 1,2,5-oxadiazol-3-yl,-4-yl, each of which is monosubstituted by R⁸ ; 1,2,4-triazol-3-yl, substituted on carbon by R¹⁰ and on N-1 by R¹¹ ; 1,2,4-triazol-5-yl or 1,2,3-triazol-4-yl or -5-yl, each substituted on carbon by R⁸ and on N-1 by R⁹ ;

X is oxygen, sulfur or NR¹ ;

R¹ is hydrogen; C₁ -C₆ -alkyl which is unsubstituted or substituted by one to five halogens and or phenyl; C₂ -C₄ -alkenyl; phenyl which is unsubstituted or substituted by one to five halogens and/or one to three of the following: C₁ -C₄ -alkyl, C₁ -C₄ -haloalkyl, C₁ -C₄ -alkoxy, C₁ -C₄ -haloalkoxy, C₁ -C₄ -alkylthio, C₁ -C₄ -haloalkylthio, nitro or cyano;

R² is halogen; cyano; thiocyano; C₁ -C₆ -alkyl which can be substituted by one to five halogens and/or one of the following: C₁ -C₄ -alkoxy, C₁ -C₄ -haloalkoxy, C₁ -C₄ -alkylthio, C₁ -C₄ -haloalkylthio, phenyl, phenoxy or phenylthio, where each of the phenyls can be substituted by one to five halogens and/or one to three of the following: C₁ -C₄ -alkyl, C₁ -C₄ -haloalkyl, C₁ -C₄ -alkoxy, C₁ -C₄ -haloalkoxy, C₁ -C₄ -alkylthio or C₁ -C₄ -haloalkylthio; C₃ -C₆ -cycloalkyl, C₃ -C₈ -cycloalkoxy, C₃ -C₆ -cycloalkylthio, C₅ -C₆ -cycloalkenyl, C₅ -C₈ -cycloalkenyloxy or C₅ 614 C₆ -cycloalkenylthio, each of which may be substituted by one to five halogens and/or one to three of the following: C₁ -C₄ -alkyl, C₁ -C₄ -haloalkyl, C₁ -C₄ -alkoxy, C₁ -C₄ -haloalkoxy, C₁ -C₄ -alkylthio or C.sub. 1 -C₄ -haloalkylthio; phenyl, phenoxy, benzyloxy or benzylthio, each of which may be substituted by one to five halogens and/or one to three of the following: cyano, nitro, C₁ -C₄ -alkyl, C₁ -C₄ -haloalkyl, C₁ -C₄ -alkoxy, C₁ -C₄ -haloalkoxy, C₁ -C₄ -alkylthio or C₁ -C₄ -haloalkylthio; saturated, singly or doubly unsaturated 5-7-membered heterocycle which contains one or two nitrogen, oxygen and/or sulfur atoms and is unsubstituted or substituted by up to two of the following: halogen, cyano, nitro, C₁ -C₄ -alkyl, C₁ -C₄ -alkoxy, C₁ -C₄ -alkylthio, C₁ -C₄ -haloalkyl, C₁ -C₄ -haloalkoxy or C₁ -C₄ -haloalkylthio; C₁ -C₄ -alkoxy or C₁ -C₄ -alkylthio, C₂ -C₆ -alkenyl or C₂ -C₆ -alkenyloxy or C₂ -C₆ -alkenylthio, C₂ -C₆ -alkynyl, C₂ -C₆ -alkynyloxy or C₂ -C₆ -alkynylthio, where the said alkoxy, alkylthio, alkenyl, alkynyl, alkenyloxy(thio) and alkynyloxy(thio) may be substituted by one to five halogens and/or one of the following: C₁ -C₄ -alkoxy, C₁ -C₄ -haloalkoxy, C₁ -C₄ -alkylthio, C₁ -C₄ -haloalkylthio; phenyl, phenoxy, phenylthio, benzyloxy or benzylthio;

COR¹² ; COQR¹³ ; SO₂ NR¹⁵ R¹⁶ ; SO₂ OR¹⁷ ; OSO₂ R¹⁸ ; S(O)_(n) R¹⁹ ;

R³ is R⁶ ; COQR¹³ ; SO₂ NR¹⁵ R¹⁶ ; SO₂ OR¹⁶ ; OSO₂ R¹⁶ ; S(O)_(n) R¹⁹ ;

R⁴ is hydrogen; halogen; cyano; C₁ -C₄ -alkyl or C₁ -C₄ -alkyl substituted by one to five halogens; C₁ -C₄ -alkoxy; C₁ -C₄ -haloalkoxy; C₁ -C₄ -alkylthio; C₁ -C₄ -haloalkylthio;

R⁵ is hydrogen; nitro or R² ;

R⁶ is hydrogen; halogen; cyano; C₁ -C₄ -alkyl, C₁ -C₄ -alkyl substituted by one to five halogens and/or one of the following: C₁ -C₄ -alkoxy, C₁ -C₄ -haloalkoxy, C₁ -C₄ -alkylthio, C₁ -C₄ -haloalkylthio, OH, SH or cyano; C₁ -C₄ -alkoxy, C₁ -C₄ -alkylthio, C₁ -C₄ -haloalkoxy or C₁ -C₄ -haloalkylthio, each of which may be substituted by the following: C₁ -C₄ -alkoxy, C₁ -C₄ -haloalkoxy, C₁ -C₄ -alkylthio or C₁ -C₄ -haloalkylthio;

R⁷ is nitro; or R² ;

R⁸ is hydrogen; nitro;

or R², or two vicinal R² together form a C₃ chain or a C₄ -C₆ chain in which one methylene can be replaced by oxygen or C₁ -C₄ -alkylimino;

R⁹ is hydrogen;

C₁ -C₆ -alkyl which may be substituted by one to five halogens and/or one of the following: C₁ -C₄ -alkoxy; C₁ -C₄ -haloalkoxy; C₁ -C₄ -alkylthio; C₁ -C₄ -haloalkylthio, phenyl, phenoxy or phenylthio, it being possible for the cyclic groups to be substituted by one to five halogens and/or one to three of the following: cyano, C₁ -C₄ -alkyl, C₁ -C₄ -haloalkyl, C₁ -C₄ -alkoxy, C₁ -C₄ -haloalkoxy, C₁ -C₄ -alkylthio or C₁ -C₄ -haloalkylthio; C₃ -C₆ -cycloalkyl or C₅ -C₆ -cycloalkenyl, each of which may be substituted by one to five halogens and/or one to three of the following: C₁ -C₄ -alkyl, C₁ -C₄ -haloalkyl, C₁ -C₄ -alkoxy, C₁ -C₄ -haloalkoxy, C₁ -C₄ -alkylthio or C₁ -C₄ -haloalkylthio; phenyl which may be substituted by one to five halogens and/or one to three of the following: cyano, nitro, C₁ -C.sub. 4 -alkyl, C₁ -C₄ -haloalkyl, C₁ -C₄ -alkoxy, C₁ -C₄ -haloalkoxy, C₁ -C₄ -alkylthio or C₁ -C₄ -haloalkylthio; C₂ -C₆ -alkenyl or C₂ -C₆ -alkynyl, each of which may be substituted by one to five halogens and/or one of the following: C₁ -C₄ -alkoxy, C₁ -C₄ -haloalkoxy, C₁ -C₄ -alkylthio or C₁ -C₄ -haloalkylthio, phenyl, phenoxy, phenylthio, benzyloxy or benzylthio; COR²¹ ;

R¹⁰ is phenyl, benzyl, phenoxy, benzyloxy, phenylthio or benzylthio, each of which may be substituted by one to five halogens and/or one to three of the following: cyano, nitro, C₁ -C₄ -alkyl, C₁ -C.sub.₄ -haloalkyl, C₁ -C₄ -alkoxy, C₁ -C₄ -haloalkoxy, C₁ -C₄ -alkylthio or C₁ -C₄ -haloalkylthio;

R¹¹ is hydrogen; phenyl or benzyl, each of which may be substituted by one to five halogens and/or one to three of the following: cyano, nitro, C₁ -C₄ -alkyl, C₁ -C₄ -haloalkyl, C₁ -C₄ -alkoxy, C₁ -C₄ -haloalkoxy, C₁ -C₄ -alkylthio or C₁ -C₄ -haloalkylthio;

R¹² is C₁ -C₄ -alkyl which is unsubstituted or substituted by halogen or methoxy; C₃ -C₅ -cycloalkyl which is unsubstituted or substituted by chlorine or fluorine; C₃ -C₄ -alkenyl;

Q is oxygen or NR¹⁴ ;

R¹³ is hydrogen; C₁ -C₆ -alkyl, C₁ -C₆ -alkyl, substituted by one to three of the following: halogen, C₁ -C₄ -alkoxy, C₁ -C₄ -alkylthio, C₁ -C₄ -haloalkoxy, C₁ C₄ -alkoxy-C₁ -C₂ -alkoxy, C₃ -C.sub.₆ -cycloalkyl and/or phenyl; C₃ -C₆ -cycloalkyl, C₃ -C₆ -cycloalkyl which is substituted once to three times by C₁ -C₄ -alkyl; C₃ -C₆ -alkenyl; C₃ -C₆ -alkynyl; phenyl, phenyl substituted by one to five halogens and/or one to three of the following: cyano, nitro, C₁ -C₄ -alkyl, C₁ -C₄ -haloalkyl, C₁ -C₄ -alkoxy, C₁ -C.sub.₄ -haloalkoxy, C₁ -C₄ -alkylthio or C₁ -C₄ -haloalkylthio;

R¹⁴ is OR²⁰ ; R¹³ or forms together with another R¹³ a C₄ -C₆ -alkylene chain in which one methylene can be replaced by oxygen or C₁ -C₄ -alkylimino;

R¹⁵ is C₁ -C₄ -alkyl; C₃ C₄ -alkenyl; C₃ -C₄ -alkynyl; cyclopropylmethyl; C₃ -C₄ -cycloalkyl;

R¹⁶ is hydrogen; C₁ -C₄ -alkyl; C₃ -C₄ -alkenyl; or forms together with R¹⁵ a C₄ -C₆ alkylene chain in which one methylene can be replaced by oxygen;

R¹⁷ is C₁ -C₄ -alkyl; C₁ -C₄ -haloalkyl;

R¹⁸ is C₁ -C₄ -alkyl; N,N-dimethylamino;

R¹⁹ is C₁ -C₄ -alkyl; C₁ -C₄ -haloalkyl; C₂ -C₄ -alkoxyalkyl; C₃ -C₄ -alkenyl; C₃ -C₄ -alkynyl; C₃ -C₄ -haloalkenyl; phenyl; phenyl substituted by fluorine, chlorine, bromine, methyl or methoxy;

n is 1 or 2;

R²⁰ is hydrogen or C₁ -C₄ -alkyl;

R²¹ is R¹² ; phenyl or benzyl, each of which may be substituted by one to five halogens and/or one to three of the following: cyano, nitro, C₁ -C₄ -alkyl, C₁ -C₄ -haloalkyl, C₁ -C₄ -alkoxy, C₁ -C₄ -haloalkoxy, C₁ -C₄ -alkylthio or C₁ -C₄ -haloalkylthio;

and the environmentally compatible salts thereof.

The present invention relates to processes for preparing the novel sulfonamides and to herbicides and bioregulators containing the compounds I and to the use thereof for controlling undesired plant growth.

It has been disclosed that certain sulfonylated 1-carbamoyl-2-pyrazolines have herbicidal and/or growth-regulatory properties (EP-A-269 141). In addition, some sulfonylated bi- or tricyclic carboxamides have herbicidal and growth-regulatory activities (EP-A-244 166).

It is an object of the present invention to find sulfonamides with satisfactory properties as herbicides and/or bioregulators.

We have found that this object is achieved by the sulfonamides I which are defined in the first paragraph and are prepared as described. The present invention also relates to herbicides and agents for controlling plant growth which contain the novel compounds I, and to a process for influencing and controlling plant growth with these compounds.

The compounds of the formula I may contain one or more centers of chirality and then exist as mixtures of diastereomers. The present invention embraces both the pure enantiomers or diastereomers and the mixtures thereof.

The compounds of the formula I are able to form salts in which the hydrogen of the --SO₂ --NH-- group is replaced by an agriculturally suitable cation. These salts are generally of metals, in particular alkali metals or alkaline earth metals, but may be of alkylated ammonium or organic amines. They are preferably prepared in inert solvents such as water, methanol or acetone at 0°-100° C. Examples of bases suitable for preparing the salts according to the invention are alkali metal carbonates such as potassium carbonate, alkali metal and alkaline earth metal hydroxides, alkali metal and alkaline earth metal alcoholates, ammonia or ethanolamine.

The term alkyl in the above definitions in each case means straight-chain or branched alkyl.

Likewise, alkenyl and alkynyl mean straight-chain or branched radicals.

The term halogen means fluorine, chlorine, bromine or iodine.

Preferred compounds of the formula I are those where

A is (A1), (A2), (A7), (A8) or (A9),

W is oxygen

X is sulfur

B is 2-, 4- or 5-oxazolyl, 3-, 4- or 5-isoxazolyl, 2-, 4- or 5-thiazolyl or 3-, 4- or 5-isothiazolyl, each of these being disubstituted by R:;

2-, 4- or 5-imidazolyl or 3-, 4- or 5-pyrazolyl, each of these being disubstituted on carbon by R: and monosubstituted on nitrogen by R⁹ ;

R⁴ is hydrogen, and the environmentally compatible salts thereof.

Particularly preferred compounds of the formula I are those where

A is (A1) and

B is 3-, 4- or 5-pyrazolyl, disubstituted on carbon by R⁸ and monosubstituted on nitrogen by R⁹, and the environmentally compatible salts thereof.

The compounds of the formula I can be obtained in a wide variety of ways similar to known reaction methods. Seven processes (A to G) are explained hereinafter by way of example.

PROCESS A

Compounds of the formula I with W═O are obtained in a conventional manner (M. L. Crossley, E. H. Northey, M. E. Hultquist, J. Am. Chem. Soc. 61, (1939), 2950-2955) by reacting an appropriate sulfonamide II in an inert organic solvent in the presence of a base with an acid halide of the formula III as shown below: ##STR4## Hal in formula III is chlorine or bromine.

The solvents expediently used for these reactions are halohydrocarbons, e.g. tetrachloromethane, chloroform, methylene chloride, dichloroethane, chlorobenzene and 1,2-dichlorobenzene; ethers, e.g. diethyl ether, methyl tert-butyl ether, dimethoxyethane, diethylene glycol dimethyl ether, tetrahydrofuran and dioxane; ketones, e.g. acetone, ethyl methyl ketone and cyclohexanone; dipolar aprotic solvents, e.g. acetonitrile and N-methylpyrrolidone; aromatic compounds e.g. benzene, toluene, xylene, pyridine, quinoline or mixtures thereof.

The reaction can be carried out at from 0° C. to the reflux temperature of the particular solvent or mixture thereof.

Suitable bases are aromatic nitrogen bases such as pyridine, 4-dimethylaminopyridine or quinoline; tertiary aliphatic amines such as triethylamine, N-ethyl-N,N-diisopropylamine and N-methylmorpholine; bi- and tricyclic amines such as diazabicycloundecene (DBU) or diazabicyclooctane (DABCO) and hydroxides, hydrides, alkoxides, carbonates and bicarbonates of alkali metals and alkaline earth metals, especially sodium hydroxide, potassium hydroxide, sodium hydride, potassium hydride, calcium hydride, lithium hydride, sodium methanolate, sodium ethanolate, potassium tert-butylate, sodium carbonate, potassium carbonate, sodium bicarbonate and potassium bicarbonate. It may also be beneficial to use combinations of the abovementioned bases.

The starting materials II and III are normally employed in the stoichiometric ratio, but an excess of one of the components may be advantageous.

The molar ratio of sulfonamide II to base is generally from 1:1 to 1:3.

The concentration of the precursors in the solvent is generally from 0.1 to 5.0 mol/l, preferably 0.2 to 2.0 mol/l.

It is particularly preferable to use inert aprotic solvents such as methylene chloride, acetone or toluene with sodium hydride, sodium carbonate or potassium carbonate as bases.

PROCESS B

Compounds of the formula I with W═O are obtained in a conventional manner (J. T. Drummond, G. Johnson, Tetrahedron Lett. 29, (1988), 1653-1656) by reacting a compound of the formula IV, in the presence of activating reagents such 2-chloro-1-methylpyridinium iodide, dicyclohexylcarbodiimide or 1,1-carbonyldiimidazole, and in the presence or absence of a base, with a compound of the formula II. ##STR5## The activated carboxylic acid is expediently reacted without intermediate isolation with component II in the presence or absence of a base.

The reactions are expediently carried out in solvents such as halohydrocarbons, e.g. chloroform, methylene chloride, dichloroethane, chlorobenzene or 1,2-dichlorobenzene; ethers, e.g. diethyl ether, methyl tert-butyl ether, dimethoxyethane, diethylene glycol dimethyl ether, tetrahydrofuran or dioxane; dipolar aprotic solvents, e.g. acetonitrile; aromatic compounds, e.g. benzene, toluene or xylene or mixture thereof.

The reactions can be carried out at from -30° C. to the reflux temperature of the particular solvent or mixture thereof.

Examples of bases which are used are organic nitrogen bases such as pyridine, 4-dimethylaminopyridine, quinoline, triethylamine, N-ethyl-N,N-diisopropylamine, diazabicycloundecene (DBU) etc., and hydroxides, hydrides, alkoxides, carbonates and bicarbonates of alkali metals and alkaline earth metals, especially sodium hydroxide, potassium hydroxide, sodium hydride, potassium hydride, sodium methanolate, sodium ethanolate, potassium tert-butylate, sodium carbonate, calcium carbonate, potassium carbonate, sodium bicarbonate or potassium bicarbonate. It may also be advantageous to use combinations of the abovementioned bases.

The starting materials II and IV, and the activating reagent, are normally employed in the stoichiometric ratio, but an excess of one of the components may be advantageous.

PROCESS C

Compounds of the formula I with W═O can be obtained in a conventional manner (M. Seefelder, Chem. Ber. 96, (1963), 3243-3253) by reacting a compound of the formula V with a compound of the formula VI ##STR6## M in formula VI is hydrogen or lithium.

It is expedient to use inert solvents such as halohydrocarbons, e.g. chloroform, methylene chloride, dichloroethane, chlorobenzene or 1,2-dichlorobenzene; ethers, e.g. tetrahydrofuran, dioxane, dimethoxyethane, diethylene glycol dimethyl ether; aromatic compounds, e.g. benzene, toluene, xylene or nitrobenzene, or mixtures thereof.

The reactions can be carried out at from -78° C. to the reflux temperature of the particular solvent or mixture thereof.

The precursors V and VI are normally employed in the stoichiometric ratio, but an excess of one of the components may be advantageous in a few cases.

PROCESS D

Compounds of the formula I with W═O can be obtained in a conventional manner (GB-2 092 136) by reacting a compound of the formula VII with a compound of the formula VIII in the presence of a strong base. ##STR7## It is expedient to polar, aprotic solvents, e.g. acetonitrile, nitromethane, nitroethane, nitrobenzene, pyridine, benzonitrile, N,N-dimethylformamide, N,N-diethylformamide, N,N-dimethylacetamide, dimethyl sulfoxide, N-methylpyrrolidone, dioxane, tetrahydrofuran, dimethoxyethane, diethylene glycol dimethyl ether or mixtures thereof.

The reactions are usually carried out at from -20° C. to the reflux temperature of the particular solvent or mixture thereof.

The bases normally used are inorganic bases such as oxides, hydroxides, hydrides, carbonates, bicarbonates and alkali metal alkoxides, especially sodium oxide, lithium oxide, potassium oxide, sodium hydroxide, potassium hydroxide, sodium hydride, potassium hydride, calcium hydride, sodium methanolate, sodium ethanolate, potassium tert-butylate, sodium carbonate, potassium carbonate, sodium bicarbonate and potassium bicarbonate. It may also be advantageous to use combinations of the abovementioned bases.

As a rule, the starting materials VII and VIII and the base are employed in the stoichiometric ratio, but an excess of one of the components may be advantageous.

PROCESS E

Compounds of the formula I with W═O are obtained in a conventional manner (M. M. Kremlev, V. G. Dolyuk, J. Org. Chem. (USSR) 10, (1974), 671-672) by reacting a compound of the formula IX and a compound of the formula X with a compound of the formula XI, ##STR8## where T is alkali metal and Hal is chlorine or bromine.

It is expedient to use inert solvents such as halohydrocarbons, e.g. chloroform, methylene chloride, dichloroethane, tetrachloromethane, chlorobenzene or 1,2-dichlorobenzene; aromatic compounds, e.g. benzene, toluene, xylene or nitrobenzene or mixtures thereof. The reactions can be carried out at from 0° C. to the reflux temperature of the particular solvent or mixture thereof.

The precursors are normally employed in the stoichiometric ratio, but an excess of one of the components may be advantageous in a few cases.

PROCESS F

Compounds of the formula I with W═S are obtained by processes similar to those disclosed in the literature (S. Scheibye, B. S. Pederson, S. O. Lawesson, Bull. Soc. Chim. Belg. 87, (1978), 229-238) by reacting a compound of the formula I obtained by process A to E with the compound of the formula XII ##STR9## in an inert aprotic solvent such as benzene, toluene, xylene, HMPA, dimethoxyethane or diethylene glycol dimethyl ether or mixtures thereof.

The reaction can be carried out at from about 0° C. to the reflux temperature of the particular solvent or mixture thereof.

The starting materials I (W═O) and XII are normally employed in the stoichiometric ratio, but an excess of one component may be advantageous.

PROCESS G

Compounds of the formula I are obtained by processes known from the literature or similar thereto (T. L. Gilchrist, Heterocyclic Chemistry, Pitman Publisher, London (1985)) by reacting a compound of the formula XIII obtained by process A to E with a nucleophile ##STR10## where the heterocycle B' carries a C-bonded substituent which acts as leaving group. This entails the leaving group, such as phenolate, chloride, bromide, etc., being replaced by the nucleophile unit.

Examples of nucleophiles which can be used are alcoholates, thiolates, hydrides and alkali metal alkyls.

It is expedient to use, appropriate for the particular nucleophile, polar aprotic solvents such as dimethyl sulfoxide (DMSO), dimethylformamide (DMF), polar solvents such as alcohols, water, etc., inert solvents such as diethyl ether, methyl tert-butyl ether, tetrahydrofuran (THF), dioxane, dimethoxyethane and diethylene glycol dimethyl ether or mixtures thereof.

The reactions are normally carried out at from -78° C. to the reflux temperature of the particular solvent or mixture thereof.

As a rule, the starting materials are employed in the stoichiometric ratio, but an excess of one of the components may be advantageous.

The sulfonamides of the formula II employed in processes A and B are in many cases commercially available. Novel sulfonamides of the formula II can be prepared by conventional methods (S. Pawlenko in Methoden der organischen Chemie, Houben-Weyl, vol. E 11/II, pages 1098 et seq. 4th edition, Thieme Verlag, Stuttgart 1985).

The acid halides of the formula III used in process A can be prepared in a conventional manner (M. F. Ansell, in The Chemistry of acyl halides (ed. S. Patai), pages 35 et seq., 1st edition, Interscience Publishers, London (1972)) from the corresponding carboxylic acids (IV) ##STR11## or the salts thereof, with organic acid halides such as oxalyl chloride, phosgene or benzoyl chloride or with inorganic acid halides such as POHal₃, PHal₃, PHal₅, SOCl₂, P(C₆ H₅)₃ Hal₂ etc. or binary systems such as P(C₆ H₅)₃ /CCl₄ etc.

It may in some cases be expedient to add a suitable base, especially organic nitrogen bases such as pyridine, 2,6-lutidine or triethylamine, or a suitable catalyst such as dimethylformamide or 4-dimethylaminopyridine.

The carboxylic acids of the formula IV are known from the literature or can be prepared by methods similar to those disclosed in the literature (R. Sustmann, H. G. Korth in Methoden der organischen Chemie, Houben-Weyl, vol. E 5/I, pages 193 et seq., 4th edition, Thieme Verlag, Stuttgart 1985).

The sulfonyl isocyanates of the formula V are prepared by standard processes known to those skilled in the art (Newer Methods of Preparative Organic Chemistry, vol. VI, pages 223 et seq., Academic Press, New York).

The compounds of the formula VI required for process C can likewise be prepared by standard processes.

The sulfonyl chlorides of the formula VII employed for process D are in many cases commercially available. Novel sulfonyl chlorides of the formula VII can be prepared by processes known to those skilled in the art (S. Pawlenko in Methoden der organischen Chemie, Houben-Weyl, vol. E 11/I, pages 1067 et seq., 4th edition, Thieme Verlag, Stuttgart 1985).

Compounds of the formula VIII are known from the literature or can be prepared by known methods (D. Deopp, H. Dopp in Methoden der organischen Chemie, Houben-Weyl, vol. E 5/II, pages 934 et seq., 4th edition, Thieme Verlag, Stuttgart 1985).

The salts of the formula IX are prepared by standard processes (F. Muth in Methoden der organischen Chemie, Houben-Weyl, vol. 9, pages 629 et seq., 4th edition, Thieme Verlag, Stuttgart 1955).

The halosulfonamides of the formula X are likewise known from the literature or can be prepared in a conventional manner (F. Muth in Methoden der organischen Chemie, Houben-Weyl, vol. 9, pages 641 et seq., 4th edition, Thieme Verlag, Stuttgart 1955).

The aldehydes of the formula XI can be synthesized by known processes (O. Bayer in Methoden der organischen Chemie, Houben-Weyl, vol. 7/1, 4th edition, Thieme Verlag, Stuttgart 1954; vol. E3, 4th edition, Thieme Verlag, Stuttgart 1983).

With a view to the intended use, the preferred compounds of the formula I have substituents with the following meanings:

X is oxygen, sulfur or NR¹,

R¹ is hydrogen; C₁ C₆ -alkyl, especially C₁ -C₄ -alkyl such as methyl, ethyl, propyl, 1-methylethyl, butyl, 1-methylpropyl, 2-methylpropyl and 1,1-dimethylethyl, which is unsubstituted or substituted by 1 to 5, in particular 1 to 3, halogens such as fluorine, chlorine or bromine and/or by phenyl. C₂ -C₄ -alkenyl, such as ethenyl, 1-propenyl, 2-propenyl, 1-methylethenyl, 1-butenyl, 2-butenyl, 3-butenyl, 1-methyl-1-propenyl, 2-methyl-2-propenyl, 1-methyl-2-propenyl, 2-methyl-1-propenyl, phenyl or phenyl substituted by 1 to 5 halogens such as fluorine, chlorine or bromine and/or one to three of the initially mentioned substituents.

R² is halogen such as fluorine, chlorine, bromine or iodine, especially fluorine, chlorine and bromine, cyano and thiocyano; C₁ -C₆ -alkyl such as methyl, ethyl, propyl, 1-methylethyl, butyl, 1-methylpropyl, 2-methylpropyl, 1,1-dimethylethyl, pentyl, 1-methylbutyl, 2-methylbutyl, 3-methylbutyl, 2,2-dimethylpropyl, 1-ethylpropyl, hexyl, 1,1-dimethylpropyl, 1,2-dimethylpropyl, 1-methylpentyl, 2-methylpentyl, 3-methylpentyl, 4-methylpentyl, 1,1-dimethylbutyl, 1,2-dimethylbutyl, 1,3-dimethylbutyl, 2,2-dimethylbutyl, 2,3-dimethylbutyl, 3,3-dimethylbutyl, 1-ethylbutyl, 2-ethylbutyl, 1,1,2-trimethylpropyl, 1,2,2-trimethylpropyl, 1-ethyl-methylpropyl and 1-ethyl-2-methylpropyl which is substituted by 1 to 5 halogens, especially fluorine, chlorine or bromine, and/or by one of the following: C₁ -C₄ -alkoxy or C₁ -C₄ -alkylthio, such as methoxy, ethoxy, propoxy, 1-methylethoxy, butoxy, 1-methylpropoxy, 2-methylpropoxy, 1,1-dimethylethoxy and the corresponding alkylthios, which may be substituted by halogen, especially fluorine, chlorine or bromine, or phenyl, phenoxy, phenylthio, optionally substituted by one to five halogens, especially fluorine, chlorine and bromine and/or one to three C₁ -C₄ -alkyl or C₁ -C₄ -alkoxy radicals; C₃ -C₆ -cycloalkyl and C₃ -C₆ -cycloalkylthio, such as cyclopropyl, cyclobutyl, cyclopentyl and cyclohexyl, especially cyclopropyl, cyclopentyl, cyclohexyl, which can carry one to five halogens, especially fluorine, chlorine and bromine, and/or one to three of the following: C₁ -C₄ -alkyl, C₁ -C.sub.₄ -haloalkyl, C₁ -C₄ -alkoxy, C₁ -C₄ -haloalkoxy, C₁ -C₄ -alkylthio, C₁ -C₄ -haloalkylthio, especially methyl, and the corresponding cycloalkylthio radicals; C₃ -C₈ -cycloalkoxy such as cyclopropoxy, cyclobutoxy, cyclopentoxy, cyclohexoxy, cycloheptoxy, cyclooctoxy, especially cyclopropoxy, cyclopentoxy and cycloheptoxy, which can be substituted by one to five halogens, especially fluorine, chlorine and bromine, and/or one to three of the following: C₁ -C₄ -alkyl, C₁ -C₄ -haloalkyl, C₁ -C₄ -haloalkoxy, C₁ -C₄ -alkylthio and C₁ -C₄ -haloalkylthio, especially methyl; C₅ -C₆ -cycloalkenyl such as 1-cyclopentenyl, 2-cyclopentenyl, 3-cyclopentenyl, 1-cyclohexenyl, 2-cyclohexenyl or 3-cyzlohexenyl, which can be substituted by one to five halogens, especially fluorine, chlorine or bromine, and/or one to three of the following: C₁ -C₄ -alkyl, C₁ -C₄ -haloalkyl, C₁ -C₄ -alkoxy, C₁ -C₄ -haloalkoxy, C₁ -C₄ -haloalkylthio and C₁ -C₄ -alkylthio especially methyl; C₅ -C₈ -cycloalkenyloxy or C₅ -C₆ -cycloalkenylthio, such as 1-cyclopentenyloxy, 2-cyclopentenyloxy, 3-cyclopentenyloxy, 1-cyclohexenyloxy, 2-cyclohexenyloxy, 3-cyclohexenyloxy, 1-cycloheptenyloxy, 2-cycloheptenyloxy, 3-cycloheptenyloxy, 4-cycloheptenyloxy, 1-cyclooctenyloxy, 2-cyclooctenyloxy, 3-cyclooctenyloxy, 4-cyclooctenyloxy, which can carry one to five of the following: fluorine, chlorine, bromine or iodine, especially fluorine, chlorine or bromine, and/or one to three of the following: C₁ -C₄ -alkyl, C₁ -C₄ -haloalkyl, C₁ -C₄ -alkoxy, C₁ -C₄ haloalkoxy, C₁ -C₄ -alkylthio or C₁ -C₄ -haloalkylthio, especially methyl; phenyl, phenoxy, benzyloxy or benzylthio, each of which can be substituted by 1 to 5 halogens, especially fluorine, chlorine or bromine, and/or one to three of the following: cyano, nitro, C₁ -C₄ -alkyl, C₁ -C₄ -haloalkyl, C₁ -C₄ -alkoxy, C₁ -C₄ -haloalkoxy, C₁ -C₄ -alkylthio and C₁ -C₄ -haloalkylthio; saturated, singly or doubly unsaturated 5-7-membered heterocycle containing one or two nitrogen, oxygen and/or sulfur atoms, e.g. thiophene, furan, isoxazole, pyrazole, thiazole, oxazole, oxadiazole, thiadiazole, tetrahydrofuran or tetrahydropyran, where the heterocyclic heteroaromatic radicals can be substituted once or twice by the following: halogen such as fluorine, chlorine, bromine or iodine, especially fluorine, chlorine and bromine, cyano, nitro, C₁ -C₄ -alkyl, C₁ -C₄ -alkoxy, C₁ -C₄ -alkythio, such as methyl, ethyl, propyl, 1-methylethyl, butyl, 1-methylpropyl, 2-methylpropyl or 1,1-dimethylethyl, which can be substituted by one to five halogens, especially fluorine, chlorine and bromine, and the corresponding alkoxy and alkylthio radicals; C₁ -C₄ -alkoxy or alkylthio such as methoxy, ethoxy propoxy, 1-methylethoxy, butoxy, 1-methylpropoxy, 2-methylpropoxy or 1,1-dimethylethoxy, which can be substituted by one to five halogens, especially fluorine, chlorine or bromine, and/or by one of the following: C₁ -C₄ -alkoxy, C₁ -C₄ -haloalkoxy, C₁ -C₄ -alkylthio or C₁ -C₄ -haloalkylthio, and the corresponding alkylthio radicals; C₃ -C₆ -alkenyl, alkenyloxy or alkenylthio such as ethenyl, 1-propenyl, 2-propenyl, 1-methylethenyl, 1-butenyl, 2-butenyl, 3-butenyl, 1-methyl-1-propenyl, 2-methyl-1-propenyl, 1-methyl-2-propenyl, 2-methyl-2-propenyl, 1-pentenyl, 2-pentenyl, 3-pentenyl, 1-methyl-1-butenyl, 2-methyl-1-butenyl, 3-methyl-1-butenyl, 1-methyl-2-butenyl, 2-methyl-2-butenyl, 3-methyl-2-butenyl, 1-methyl-3-butenyl, 2-methyl-3-butenyl, 3-methyl-3-butenyl, 1,1-dimethyl-2-propenyl, 1,2-dimethyl-1-propenyl, 1,2-dimethyl-2-propenyl, 1-ethyl-1-propenyl, 1-ethyl-2-propenyl, 1-hexenyl, 2-hexenyl, 3-hexenyl, 4-hexenyl, 5-hexenyl, 1-methyl-1-pentenyl, 2-methyl-1-pentenyl, 3-methyl-1-pentenyl, 4-methyl-1 -pentenyl, 1-methyl-2-pentenyl, 2-methyl-2-pentenyl, 3-methyl-2-pentenyl, 4-methyl-2-pentyl, 1-methyl-3-pentenyl, 2-methyl-3-pentenyl, 3-methyl-3-pentenyl, 4-methyl-3-pentenyl, 1-methyl-4-pentenyl, 2-methyl-4-pentenyl, 3-methyl-4-pentenyl, 4-methyl-4-pentenyl, 1,1-dimethyl-2-butenyl, 1,1,-dimethyl-3-butenyl, 1,2-dimethyl-1-butenyl, 1,2-dimethyl-2-butenyl, 1,2-dimethyl-3-butenyl, 1,3-dimethyl-1-butenyl, 1,3-dimethyl-2-butenyl, 1,3-dimethyl-3-butenyl, 2,2-dimethyl-3-butenyl, 2,3-dimethyl-1-butenyl, 2,3-dimethyl-2-butenyl, 2,3-dimethyl-3-butenyl, 3,3-dimethyl-1-butenyl, 1-ethyl-1-butenyl, 1-ethyl-2-butenyl, 1-ethyl-3-butenyl, 2-ethyl-1-butenyl, 2-ethyl-2-butenyl, 2-ethyl-3-butenyl, 1,1,2-trimethyl-2-propenyl, 1-ethyl-1-methyl-2-propenyl, 1-ethyl-2-methyl-1-propenyl and 1-ethyl-2-methyl-2-propenyl, which can be substituted by one to five halogens, especially fluorine, chlorine or bromine, and/or by one of the following: C₁ -C₄ -alkoxy, C₁ -C₄ -haloalkoxy, C₁ -C₄ -alkylthio or C₁ 614 C₄ -haloalkylthio, and the corresponding alkenyloxy and alkenylthio radicals; C₂ -C₆ -alkynyl, alkynyloxy or alkynylthio, such as ethynyl, 1-propynyl, 2-propynyl, 1-butynyl, 2-butynyl, 3-butynyl, 1-methyl-2-propynyl, 1-pentynyl, 2-pentynyl, 3-pentynyl, 4-pentynyl, 1-methyl-2-butynyl, 1-methyl-3-butynyl, 2-methyl-3-butynyl, 3-methyl-1-butynyl, 1,1-dimethyl-2-propynyl, 1-ethyl-2-propynyl, 1-hexynyl, 2-hexynyl, 3-hexynyl, 4-hexynyl, 5-hexynyl, 1-methyl-2-pentynyl, 1-methyl-3-pentynyl, 1-methyl-4-pentynyl, 2-methyl-3-pentynyl, 2-methyl-4-pentynyl, 3-methyl-1-pentynyl, 3-methyl-4-pentynyl, 4-methyl-1-pentynyl, 4-methyl-2-pentynyl, 1,1-dimethyl-2-butynyl, 1,1-dimethyl-3-butynyl, 1,2-dimethyl-3-butynyl, 2,2-dimethyl-3-butynyl, 3,3-dimethyl-1-butynyl, 1-ethyl-2-butynyl, 1-ethyl-3-butynyl, 2-ethyl-3-butynyl and 1-ethyl-1-methyl-2-propynyl, which can be substituted by one to five halogens, especially fluorine, chlorine or bromine, and/or by one of the following: C₁ -C₄ -alkoxy, C₁ -C₄ -haloalkoxy, C₁ -C₄ -alkylthio or C₁ -C.sub.₄ -haloalkylthio, and the corresponding alkynyloxy and alkynylthio radicals; COR¹² such as alkylcarbonyl with C₁ -C₄ -alkyl as mentioned for R¹², such as cycloalkylcarbonyl with C₃ -C₅ -cycloalkyl as mentioned for R¹², such as alkenylcarbonyl with C₃ -C₄ -alkenyl as mentioned for R¹², especially methylcarbonyl, ethylcarbonyl and cyclopropylcarbonyl; COQR¹³ such as carboxyl, such as alkoxycarbonyl with C₁ -C₆ -alkyl as mentioned for R¹³, cycloalkoxycarbonyl with C₃ -C₆ -cycloalkyl as mentioned for R¹³, such as alkenyloxycarbonyl with C₃ -C₆ -alkenyl as mentioned for R¹³ such as alkynyloxycarbonyl with C₃ -C₆ -alkynyl as mentioned for R¹³, such as phenoxycarbonyl with phenyl as mentioned for R¹³, such as carboxamide, such as N-alkylaminocarbonyl with C₁ -C₆ -alkyl as mentioned for R¹³, such as N-cycloalkylaminocarbonyl with C₃ -C₆ -cycloalkyl as mentioned for R¹³, such as N-alkenylaminocarbonyl with C₃ -C₆ -alkenyl as mentioned for R¹³, such as N-alkynylaminocarbonyl with C₃ -C₆ -alkynyl as mentioned for R¹³, such as N-phenylaminocarbonyl with phenyl as mentioned for R¹³, such as N,N-dialkylaminocarbonyl with C₃ -C₆ -alkyl as mentioned for R¹³, such as N-alkyl-N-cycloalkylaminocarbonyl with C₃ -C₆ -alkyl as mentioned for R¹³ and C₁ -C.sub.₆ -cycloalkyl as mentioned for R¹³, such as N-alkyl-N-phenylaminocarbonyl with C₁ -C₁₆ -alkyl as mentioned for R¹³ and phenyl as mentioned for R¹³, such as N-alkoxyaminocarbonyl with alkoxy as described for R¹⁴, such as 1-azacycloalkylcarbonyl with 1-azacycloalkyl as described for R¹⁴, especially methoxycarbonyl, ethoxycarbonyl, isopropoxycarbonyl, N-methylaminocarbonyl, and N,N-dimethylaminocarbonyl; SO₂ NR¹⁵ R¹⁶ such as N-alkylaminosulfonyl with C₁ -C₄ -alkyl as described for R¹⁵, such as N-alkenylaminosulfonyl with C₃ -C₄ -alkenyl as described for R¹⁵, such as N-alkynylaminosulfonyl with C₃ -C₄ -alkynyl as described for R¹⁵, such as N-cyclopropylmethylaminosulfonyl, such as N-cycloalkylaminosulfonyl with C₃ -C₄ -cycloalkyl as described for R¹⁵, such as N,N-dialkylaminosulfonyl with C₁ -C₄ -alkyl as described for R¹⁵ and with C₁ -C₄ -alkyl as described for R¹⁶, such as N-alkyl-N-alkenylaminosulfonyl with C₁ -C₄ -alkyl as described for R¹⁵ and C₃ -C₄ -alkenyl as described for R¹⁶, such as N-alkyl-N-alkynylaminosulfonyl with C₁ -C₄ -alkyl as described for R¹⁶ and C₃ -C₄ -alkynyl as mentioned for R¹⁵, such as N-alkyl-N-cyclopropylmethylaminosulfonyl with C₁ -C.sub.₄ -alkyl as described for R¹⁶, such as N-alkyl-N-cycloalkylaminosulfonyl with C₁ -C₄ -alkyl as mentioned for R¹⁶ and C₃ -C₄ -cycloalkyl as described for R¹⁵, such as 1-azacycloalkylsulfonyl with 1-azacycloalkyl as described for R¹⁶, especially N,N-dimethylaminosulfonyl and N,N-diethylaminosulfonyl; SO₂ OR¹⁷ such as alkoxysulfonyl with C₁ -C₄ -alkyl as described for R¹⁷, such as haloalkoxysulfonyl with C₁ -C₄ -haloalkyl as described for R¹⁷, especially methoxysulfonyl, ethoxysulfonyl and isopropoxysulfonyl; OSO₂ R¹⁸ such as alkylsulfonyloxy with C₁ -C₄ -alkyl as described for R¹⁸, such as N,N-dimethylsulfonyloxy, especially methylsulfonyloxy and ethylsulfonyloxy; S(O)_(n) R¹⁹ such as alkylsulfonyl with C₁ -C₄ -alkyl as described for R¹⁹, such as haloalkylsulfonyl with C₁ -C₄ -haloalkyl as described for R¹⁹, such as alkoxyalkylsulfonyl with C₂ -C₄ -alkoxyalkyl as described for R¹⁹, such as alkenylsulfonyl with C₃ -C₄ -alkenyl as mentioned for R¹⁹, such as alkynylsulfonyl with C₃ -C₄ -alkynyl as described for R¹⁹, such as C₃ -C₄ -haloalkenylsulfonyl with C₃ -C₄ -haloalkenyl as described for R¹⁹, such as phenylsulfonyl with phenyl as described for R¹⁹, such alkylsulfinyl with C₁ -C₄ -alkyl as mentioned for R¹⁹, such as haloalkylsulfinyl with C₁ -C₄ -haloalkyl as described for R¹⁹, such as phenylsulfinyl with phenyl as described for R¹⁹, especially methylsulfonyl, ethylsulfonyl, isopropylsulfonyl, propylsulfonyl, methylsulfinyl, and ethylsulfinyl.

R³ is R₆, especially methyl, ethyl, trifluoromethyl, chloromethyl, methoxymethyl, methylthiomethyl, methoxy, ethoxy, isopropoxy, trifluoromethoxy, difluoromethoxy, chlorodifluoromethoxy, 2,2,2-trifluoroethoxy, 2-chloroethoxy, 2-methoxyethoxy, methylthio and ethylthio; chlorodifluoromethoxy, 2,2,2-trifluoroethoxy, 2-chloroethoxy, 2-methoxyethoxy, methylthio and ethylthio; COQR¹³ such as carboxyl, such as alkoxycarbonyl with C₁ -C₆ -alkyl as mentioned for R¹³, cycloalkoxycarbonyl with C₃ -C₆ -cycloalkyl as mentioned for R¹³ such as alkenyloxycarbonyl with C₃ -C₆ -alkenyl as mentioned for R¹³, such as alkynyloxycarbonyl with C₃ -C.sub.₆ -alkynyl as mentioned for R¹³, such as phenoxycarbonyl with phenyl as mentioned for R¹³, such as carboxamide, such as N-alkylaminocarbonyl with C₁ -C₆ -alkyl as mentioned for R¹³, such as N-cycloalkylaminocarbonyl with C₃ -C₆ -cycloalkyl as mentioned for R¹³, such as N-alkenylaminocarbonyl with C₃ -C₆ -alkenyl as mentioned for R¹³, such as N-alkynylaminocarbonyl with C₃ -C₆ -alkynyl as mentioned for R¹³, such as N-phenylaminocarbonyl with phenyl as mentioned for R¹³, such as N,N-dialkylaminocarbonyl with C₃ -C₆ -alkyl as mentioned for R¹³ , such as N-alkyl-N-cycloalkylaminocarbonyl with C₃ -C₆ -alkyl as mentioned for R¹³ and C₃ -C₆ -cycloalkyl as mentioned for R¹³, such as N-alkyl-N-phenylaminocarbonyl with C₁ -C₆ -alkyl as mentioned for R¹³ and phenyl as mentioned for R¹³, such as N-alkoxyaminocarbonyl with alkoxy as described for R¹⁴, such as 1-azacycloalkylcarbonyl with 1-azacycloalkyl as described for R¹⁴, especially methoxycarbonyl, ethoxycarbonyl, isopropoxycarbonyl, N-methylaminocarbonyl, and N,N-dimethylaminocarbonyl; SO₂ NR¹⁵ R¹⁶ such as N-alkylaminosulfonyl with C₁ -C₄ -alkyl as described for R¹⁵, such as N-alkenylaminosulfonyl with C₃ -C₄ -alkenyl as described for R¹⁵, such as N-alkynylaminosulfonyl with C₃ -C₄ -alkynyl as described for R¹⁵, such as N-cyclopropylmethylaminosulfonyl, such as N-cycloalkylaminosulfonyl with C₃ -C₄ -cycloalkyl as described for R¹⁵, such as N,N-dialkylaminosulfonyl with C₁ -C₄ -alkyl as described for R¹⁵ and with C₁ -C₄ -alkyl as described for R¹⁶, such as N-alkyl-N-alkenylaminosulfonyl with C₁ -C₄ -alkyl as described for R¹⁵ and C₃ -C₄ -alkenyl as described for R¹⁶, such as N-alkyl-N-alkynylaminosulfonyl with C₁ -C₄ -alkyl as described for R¹⁶ and C₃ -C₄ -alkynyl as mentioned for R¹⁵, such as N-alkyl-N-cyclopropylmethylaminosulfonyl with C₁ -C₄ -alkyl as described for R¹⁶, such as N-alkyl-N-cycloalkylaminosulfonyl with C₁ -C₄ -alkyl as mentioned for R¹⁶ and C₃ -C₄ -cycloalkyl as described for R¹⁵, such as 1-azacycloalkylsulfonyl with 1-azacycloalkyl as described for R¹⁶, especially N,N-dimethylaminosulfonyl and N,N-diethylaminosulfonyl; SO₂ OR¹⁷ such as alkoxysulfonyl with C₁ -C₄ -alkyl as described for R¹⁷, such as haloalkoxysulfonyl with C₁ -C₄ -haloalkyl as described for R¹⁷, especially methoxysulfonyl, ethoxysulfonyl and isopropoxysulfonyl; OSO₂ R¹⁸ alkylsulfonyloxy with C₁ -C₄ -alkyl as described for R¹⁸, such as N,N-dimethylsulfonyloxy, especially methylsulfonyloxy and ethylsulfonyloxy; S(O)_(n) R¹⁹ such as alkylsulfonyl with C₁ -C₄ -alkyl as described for R¹⁹, such as haloalkylsulfonyl with C₁ -C₄ -haloalkyl as described for R¹⁹, such as alkoxyalkylsulfonyl with C₂ -C₄ -alkoxyalkyl as described for R¹⁹, such as alkenylsulfonyl with C₃ -C₄ -alkenyl as mentioned for R¹⁹, such as alkynylsulfonyl with C₃ -C₄ -alkynyl as described for R¹⁹, such as C₃ -C₄ -haloalkenylsulfonyl with C₃ -C₄ -haloalkenyl as described for R¹⁹, such as phenylsulfonyl with phenyl as described for R¹⁹, such alkylsulfinyl with C₁ -C₄ -alkyl as mentioned for R¹⁹, such as haloalkylsulfinyl with C₁ -C₄ -haloalkyl as described for R¹⁹, such as phenylsulfinyl with phenyl as described for R¹⁹, especially methylsulfonyl, ethylsulfonyl, isopropylsulfonyl, propylsulfonyl, methylsulfinyl, and ethylsulfinyl.

R⁴ is hydrogen, halogen, especially fluorine, chlorine or bromine, cyano, C₁ -C₄ -alkyl, C₁ -C₄ -alkoxy or C₁ -C₄ -alkylthio, such as methyl, ethyl, propyl, 1-methylethyl, butyl, 1-methylpropyl, 2-methylpropyl or 1,1-dimethylethyl, which can be substituted by one to five halogens, especially fluorine, chlorine or bromine, and the corresponding alkoxy and alkylthio radicals, especially methyl, ethyl, fluoromethyl, difluoromethyl, trifluoromethyl, pentafluoroethyl, methoxy, ethoxy, chloromethoxy, dichloromethoxy, trichloromethoxy, fluoromethoxy, difluoromethoxy,chlorodifluoromethoxy,trifluoromethoxy, dichlorofluoromethoxy, 2-fluoroethoxy, 2,2-difluoroethoxy, 2,2,2-trifluoroethoxy, 2-chloro-2-fluoroethoxy, 2-chloro-2,2-difluoroethoxy, 2,2-dichloro-2-fluoroethoxy, 2,2,2-trichloroethoxy, pentafluoroethoxy and 2-chloroethoxy;

R⁵ is hydrogen; nitro or R², especially fluorine, chlorine, bromine, methyl, ethyl, trifluoromethyl, methoxy, ethoxy, 2-chloroethoxy, 2-methoxyethoxy, trifluoromethoxy, methoxycarbonyl, ethoxycarbonyl, N,N-dimethylaminocarbonyl, methylsulfinyl, ethylsulfinyl, methylsulfonyl, ethylsulfonyl, N-isopropylaminosulfonyl and N,N-dimethylaminosulfonyl;

R⁶ is hydrogen; halogen such as fluorine, chlorine, bromine or iodine, especially fluorine, chlorine and bromine; cyano; C₁ -C₄ -alkyl such as methyl, ethyl, propyl, 1-methylethyl, butyl, 1-methylpropyl, 2-methylpropyl and 1,1-dimethylethyl, which can be substituted by one to five halogens especially fluorine, chlorine or bromine and/or one of the following: hydroxyl, mercapto, cyano, C₁ -C₄ -alkoxy, C₁ -C₄ -alkylthio, such as methoxy, ethoxy, propoxy, butoxy, 1-methylethoxy, 1-methylpropoxy, 2-methylpropoxy or 1,1-dimethylethoxy, which can be substituted by one to five halogens, especially fluorine, chlorine or bromine, and the corresponding alkylthio radicals, especially methyl, ethyl, trifluoromethyl, chloromethyl, methoxymethyl and methylthiomethyl; C₁ -C₄ -alkoxy, C₁ -C₄ -alkylthio, such as methoxy, ethoxy, propoxy, butoxy, 1-methylethoxy, 1-methylpropoxy, 2-methylpropoxy or 1,1-dimethylethoxy, which can be substituted by one to five halogens, especially fluorine, chlorine or bromine, and/or by the following: C₁ -C₄ -alkoxy, C₁ -C₄ -alkylthio, such as methoxy, ethoxy, propoxy, butoxy, 1-methylethoxy, 1-methylpropoxy, 2-methylpropoxy and 1,1-dimethylethoxy, which can be substituted by halogens, especially fluorine, chlorine or bromine, and the corresponding alkylthio radicals, especially methoxy, ethoxy, isopropyloxy, trifluoromethoxy, 2,2,2-trifluoroethoxy, difluoromethoxy, 2-chloroethoxy, 2-methoxyethoxy, methylthio and ethylthio;

R⁷ is nitro or R², especially fluorine, chlorine, bromine, methyl, ethyl, chloromethyl, fluoromethyl, difluoromethyl, chlorodifluoromethyl, trifluoromethyl, dichlorofluoromethyl, methoxymethyl, methoxycarbonyl, N,N-dimethylaminocarbonyl and ethoxycarbonyl;

R⁸ is hydrogen, nitro or R², especially fluorine, chlorine, bromine, iodine, cyano, nitro, methyl, ethyl, propyl, 1-methylethyl, butyl, 1-methylpropyl, 2-methylpropyl and 1,1-dimethylethyl, fluoromethyl, chloromethyl, bromomethyl, difluoromethyl, trifluoromethyl, trichloromethyl, 2-fluoroethyl, 2-chloroethyl, 2,2-difluoroethyl, 2,2,2-trifluoroethyl, 2,2,2-trichloroethyl, pentafluoroethyl, methoxymethyl, 2-mathoxyethyl, 1-methoxyethyl, 2-methoxy-1-methylethyl, ethoxymethyl, benzyl, cyclopropyl, cyclopentyl, cyclohexyl, phenyl, 2-methylphenyl, 3-methylphenyl, 4-methylphenyl, 2-trifluoromethylphenyl, 3-trifluoromethylphenyl, 4-trifluoromethylphenyl, 2-fluorophenyl, 3-fluorophenyl, 4-fluorophenyl, 2-chlorophenyl, 3-chlorophenyl, 4-chlorophenyl, 2-nitrophenyl, 3-nitrophenyl, 4-nitrophenyl, 2-methoxyphenyl, 3-methoxyphenyl, 4-methoxyphenyl, 2-tetrahydropyranyl, 3-tetrahydropyranyl, 2-tetrahydrofuranyl, 3-tetrahydrofuranyl, 2-thienyl, 3-thienyl, 2-furanyl, 3-furanyl, 1-methyl-3-pyrazolyl, 1-methyl-4-pyrazolyl, 1-methyl-5-pyrazolyl, 1-ethyl-3-pyrazolyl, 1-ethyl-4-pyrazolyl, 1-ethyl-5-pyrazolyl, methoxy, ethoxy, isopropoxy, 2-chloroethoxy, 2-methoxyethoxy, trifluoromethoxy, difluoromethoxy, chlorodifluoromethoxy, 2,2,2-trifluoroethoxy, phenoxy, benzyloxy, methylthio, ethylthio, phenylthio, benzylthio, 2-propenyl, 1-methyl-2-propenyl, 2-methyl-2-propenyl, 2-butenyl, 2-propynyl, 1-methyl-2-propynyl, 2-butynyl, methylcarbonyl, ethylcarbonyl, cyclopropylcarbonyl, chloromethylcarbonyl, bromomethylcarbonyl, fluoromethylcarbonyl, trifluoromethylcarbonyl, methoxymethylcarbonyl, carboxyl, methoxycarbonyl, ethoxycarbonyl, isopropoxycarbonyl, 2,2,2-trifluoroethoxycarbonyl, 2-methoxyethoxcarbonyl, benzyloxycarbonyl, aminocarbonyl, N-methylaminocarbonyl, N,N-dimethylaminocarbonyl, N-ethylaminocarbonyl, N,N-diethylaminocarbonyl, N-isopropylaminocarbonyl, N-benzylaminocarbonyl, N-phenylaminocarbonyl, N-methoxyaminocarbonyl, N-ethoxyaminocarbonyl, N,N-dimethylaminosulfonyl, N-methyl-N-ethylaminosulfonyl, N,N-diethylaminosulfonyl, N-methylaminosulfonyl, N-ethylaminosulfonyl, methoxysulfonyl, ethoxysulfonyl, isopropoxysulfonyl, 2-chloroethoxysulfonyl, 2,2,2-trifluoroethoxysulfonyl, methylsulfonyloxy, ethylsulfonyloxy, isopropylsulfonyloxy, N,N-dimethylaminosulfonyloxy, methylsulfinyl, ethylsulfinyl, isopropylsulfinyl, phenylsulfinyl, methylsulfonyl, ethylsulfonyl, isopropylsulfonyl or propylsulfonyl; or 2 vicinal R² radicals together form a C₃ chain such as propylene or a C₄ -C₆ chain in which one methylene can be replaced by oxygen or C₁ -C₄ -alkylamino such as methyl-, ethyl-, propyl- or butylimino;

R⁹ is hydrogen; unsubstituted or substituted C₁ -C₆ -alkyl, especially C₁ -C₄ -alkyl, such as methyl, ethyl, propyl, 1-methylethyl, butyl, 1-methylpropyl, 2-methylpropyl and 1,1-dimethylethyl, particularly suitable substituents being the following: fluorine, chlorine, bromine, C₁ -C₄ -alkoxy, especially methoxy, ethoxy, or phenyl; C₃ -C₆ -cycloalkyl or cycloalkenyl, such as cyclopropyl, cyclobutyl, cyclopentyl, cyclohexyl, 1-cyclopentenyl, 2-cyclopentenyl, 3-cyclopentenyl, 1-cyclohexenyl, 2-cyclohexenyl or 3-cyclohexenyl, each of which can be further substituted, preferably by methyl, ethyl, fluorine, chlorine or trifluromethyl; unsubstituted or substituted phenyl; C₂ -C₆ -alkenyl or C₂ -C₆ -alkynyl as mentioned for R², especially vinyl, 2-propenyl and 2-propynyl; COR²¹, especially methylcarbonyl, ethylcarbonyl and phenylcarbonyl;

R¹⁰ is unsubstituted or substituted phenyl, benzyl, phenoxy, phenylthio, benzyloxy or benzylthio, suitable and preferred substituents being fluorine, chlorine, bromine, methyl, ethyl, trifluoromethyl, methoxy and ethoxy;

R¹¹ is hydrogen; unsubstituted or substituted phenyl or benzyl, e.g. 2-substituted or 2,4-disubstituted or 2,6-disubstituted or 2,4,6-trisubstituted phenyl or benzyl, suitable substituents being the following: cyano, nitro, C₁ -C₄ -alkyl, C₁ -C₄ -haloalkyl, C₁ -C₄ -alkoxy, C₁ -C₄ - haloalkoxy, C₁ -C₄ -haloalkylthio, especially phenyl, 2-chlorophenyl, 2-fluorophenyl, 2-methylphenyl, 2-trifluoromethylphenyl, 2-mathoxyphenyl, 2,4-dichlorophenyl, 2,6-dichlorophenyl, 2,6-difluorophenyl, 2,6-dimethylphenyl, 2-chloro-4-trifluoromethylphenyl and 2,6-dichloro-4-trifluoromethylphenyl;

R¹² is C₁ -C₄ -alkyl such as methyl, ethyl, propyl, 1-methylethyl, butyl, 1-methylpropyl, 2-methylpropyl and 1,1-dimethylethyl, each of which may be substituted by halogen, especially fluorine or chlorine or by methoxy; C₃ -C₅ -cycloalkyl such as cyclopropyl, cyclobutyl or cyclopentyl, unsubstituted or substituted by chlorine or fluorine; C₃ -C₄ -alkenyl such as 1-propenyl, 2-propenyl, 1-methylethenyl, 1-butenyl, 2-butenyl, 3-butenyl, 1-methyl-1-propenyl, 2-methyl-1-propenyl or 2-methyl-2-propenyl;

Q is oxygen or NR¹⁴

R¹³ is hydrogen; C₁ -C₆ -alkyl, especially C₁ -C₄ -alkyl, such as methyl, ethyl, propyl, 1-methylethyl, butyl, 1-methylpropyl, 2-methylpropyl and 1,1-dimethylethyl, substituted alkyl e.g. by halogen, especially fluorine, chlorine or bromine, C₁ -C₄ -alkoxy, especially methoxy or ethoxy; unsubstituted or substituted C₃ -C.sub.₉ -cycloalkyl as mentioned for R⁹, unsubstituted or substituted by methyl or ethyl; C₃ -C₆ -alkenyl such as 2-propenyl, 2-butenyl, 3-butenyl, 1methyl-2-propenyl, 2-methyl-2-propenyl, 2-pentenyl, 3-pentenyl, 4-pentenyl, 1-methyl-2-butenyl, 2-methyl-2-butenyl, 3-methyl-2-butenyl, 1-methyl-3-butenyl, 2-methyl-3-butenyl, 3-methyl-3-butenyl, 1,1-dimethyl-2-propenyl, 1,2-dimethyl-2-propenyl, 1-ethyl-2-propenyl, 2-hexenyl, 3-hexenyl, 4-hexenyl, 5-hexenyl, 1-methyl-2-pentenyl, 2-methyl-2-pentenyl, 3-methyl-2-pentenyl, 4-methyl-2-pentenyl, 1-methyl-3-pentenyl, 2-methyl-3-pentenyl, 3-methyl-3-pentenyl, 4-methyl-3-pentenyl, 1-methyl-4-pentenyl, 2-methyl-4-pentenyl, 3-methyl-4-pentenyl, 4-methyl-4-pentenyl, 1,1-dimethyl-2-butenyl, 1,1,-dimethyl-3-butenyl, 1,2 -dimethyl-2-butenyl, 1,2-dimethyl-3-butenyl, 1,3-dimethyl-2-butenyl, 1,3-dimethyl-3-butenyl, 2,2-dimethyl-3-butenyl, 2,3-dimethyl-2-butenyl, 2,3-dimethyl-3-butenyl, 3,3-dimethyl-2-butenyl, 1-ethyl-2-butenyl, 1-ethyl-3-butenyl, 2-ethyl-2-butenyl, 2-ethyl-3-butenyl, 1,1,2-trimethyl-2-propenyl, 1-ethyl-1-methyl-2-propenyl and 1-ethyl-2-methyl-2-propenyl; C₃ -C₆ -alkynyl such as ethynyl, 1-propynyl, 2-propynyl, 1-butynyl, 2-butynyl, 3-butynyl, 1-methyl-2-propynyl, 1-pentynyl, 2-pentynyl, 3-pentynyl, 4-pentynyl, 1-methyl-2-butynyl, 1-methyl-3-butynyl, 2-methyl-3-butynyl, 3-methyl-1-butynyl, 1,1-dimethyl-2-propynyl, 1-ethyl-2-propynyl, 1-hexynyl, 2-hexynyl, 3-hexynyl, 4-hexynyl, 5-hexynyl, 1-methyl-2-pentynyl, 1-methyl-3-pentynyl, 1-methyl-4-pentynyl, 2-methyl-3-pentynyl, 2-methyl-4-pentynyl, 3-methyl-1-pentynyl, 3-methyl-4-pentynyl, 4-methyl-1-pentynyl, 4-methyl-2-pentynyl, 1,1-dimethyl-2-butynyl, 1,1-dimethyl-3-butynyl, 1,2-dimethyl-3-butynyl, 2,2-dimethyl-3-butynyl, 3,3-dimethyl-1-butynyl, 1-ethyl-2-butynyl, 1-ethyl-3-butynyl, 2-ethyl-3-butynyl and 1-ethyl-1-methyl-2-propynyl; unsubstituted or substituted phenyl, e.g. by halogen, especially fluorine, chlorine or bromine, C₁ -C₄ -alkyl, especially methyl or ethyl, C₁ -C₄ -haloalkyl, especially trifluoromethyl, difluoromethyl, chlorodifluoromethyl or trichloromethyl, C₁ -C₄ -alkoxy, especially methoxy or ethoxy, C₁ -C₄ -haloalkoxy, especially trifluoromethoxy, difluoromethoxy or chlorodifluoromethoxy;

R¹⁴ is OR²⁰, especially methyl or ethyl; R¹³ or forms together with R¹³ a C₄ -C₆ -alkylene chain such as butylene, pentylene or hexylene in which one methylene can be replaced by oxygen or C₁ -C₄ -alkylamino, e.g. methyl- or ethylimino;

R¹⁵ is C₁ -C₄ -alkyl such as methyl, ethyl, propyl, 1-methylethyl, butyl, 1-methylpropyl, 2-methylpropyl and 1,1-dimethylethyl; C₃ -C₄ -alkenyl or alkynyl, e.g. 2-propenyl, 2-butenyl, 3-butenyl, 1-methyl-2-propenyl, 2-methyl-2-propenyl, 2-butynyl, 2-propynyl, 3-butynyl, cyclopropylmethyl, cyclopropyl or cyclobutyl;

R¹⁶ is hydrogen; C₁ -C₄ -alkyl as mentioned for R¹⁵, C₃ -C.sub.₄ -alkenyl, e.g. 2-propenyl, 2-butenyl, 3-butenyl, 1-methyl-2-propenyl or 2-methyl-2-propenyl; a C₄ -C₆ -alkylene chain in which one methylene can be replaced by oxygen;

R¹⁷ is C₁ -C₄ -alkyl as mentioned for R¹⁵, C₁ -C₄ -haloalkyl, especially C₁ -C₂ -haloalkyl, such as chloromethyl, dichloromethyl, trichloromethyl, chlorofluoromethyl, fluoromethyl, difluoromethyl, trifluoromethyl, dichlorofluoromethyl, chlorodifluoromethyl, 1-fluoroethyl, 2-fluoroethyl, 2,2-difluoroethyl, 2,2,2-trifluoroethyl, 2-chloro-2-fluoroethyl, 2-chloro-2,2-difluoroethyl, 2,2-dichloro-2-fluoroethyl, 2,2,2-trichloroethyl and pentafluoroethyl;

R¹⁸ is C₁ -C₄ -alkyl as mentioned for R¹⁵ or N,N-dimethylamino;

R¹⁹ is C₁ -C₄ alkyl or haloalkyl as mentioned for R¹⁷, C₂ -C₄ -alkoxyalkyl such as methoxy or ethoxyethyl; C₃ -C₄ -alkenyl such as 2-propenyl, 2-butenyl, 3-butenyl, 1-methyl-2-propenyl or 2-methyl-2-propenyl, unsubstituted or substituted by halogen, especially fluorine or chlorine; C₃ -C₄ -alkynyl such as 2-propynyl, 2-butynyl or 3-butynyl; phenyl or phenyl substituted by one to three fluorine, chlorine, bromine, methyl or methoxy;

n is 1 or 2

R²⁰ is hydrogen or C₁ -C₄ -alkyl as mentioned for R¹⁵ ;

R²¹ is R¹², especially methyl, ethyl, trifluoromethyl, difluoromethyl or cyclopropyl; phenyl, benzyl, unsubstituted or substituted by, for example, halogen, especially fluorine, chlorine or bromine, cyano, C₁ -C₄ -alkyl, especially methyl or ethyl, C₁ -C₄ -alkoxy which is unsubstituted or substituted by halogen, especially methoxy, ethoxy or 2-chloroethoxy.

The herbicidal and growth-regulating compounds I according to the invention and the agents containing them can be applied, for example, in the form of directly sprayable solutions, powders, suspensions, including high percentage aqueous, oily or other suspensions or dispersions, emulsions, oily dispersions, pastes, dusting agents, broadcasting agents or granules by spraying, atomizing, dusting, broadcasting or watering. The application forms depend on the purposes for which they are used; in any event, they should ensure maximum dispersion of the active ingredients according to the invention.

The compounds I are suitable in general for preparing directly sprayable solutions, emulsions, pastes or oily dispersions. Suitable inert additives are mineral oil fractions of medium to high boiling point such as kerosine or diesel oil, also coaltar oils and oils of vegetable or animal origin, aliphatic, cyclic and aromatic hydrocarbons e.g. toluene, xylene, paraffin, tetrahydronaphthalene, alkylated naphthalenes or their derivatives, methanol, ethanol, propanol, butanol, cyclohexanol, cyclohexanone, chlorobenzene, isophorone or highly polar solvents such as N,N-dimethylformamide, dimethyl sulfoxide, N-methylpyrrolidone or water.

Aqueous application forms can be prepared from emulsion concentrates, dispersions, pastes, wettable powders or water-dispersible granules by adding water. To prepare emulsions, pastes or oily dispersions, the substances can be homogenized as such or dissolved in an oil or solvent, using wetting agents, adhesion promoters, dispersants or emulsifiers, in water. However, concentrates which are suitable for dilution with water can also be prepared from active substance, wetting agent, adhesion promoter, dispersant or emulsifier and, possibly, solvent or oil.

Suitable surfactants are the alkali metal, alkaline earth metal and ammonium salts of aromatic sulfonic acids, e.g. lignin-, phenol-, naphthalene- and dibutylnaphthalenesulfonic acid, and of fatty acids, alkyl- and alkylarylsulfonates, alkyl, lauryl ether and fatty alcohol sulfates, and salts of sulfated hexa-, hepta- and octadecanols, and of fatty alcohol glycol ethers, condensation products of sulfonated naphthalene and its derivatives with formaldehyde, condensation products of naphthalene or of naphthalenesulfonic acids with phenol and formaldehyde, polyoxyethylene octylphenol ethers, ethoxylated isooctyl-, octyl- or nonylphenol, alkylphenol and tributylphenyl polyglycol ethers, alkylaryl polyether alcohols, isotridecyl alcohol, fatty alcohol/ethylene oxide condensates, ethoxylated castor oil, polyoxyethylene alkyl ethers or polyoxypropylene, lauryl alcohol polyglycol ether acetate, sorbitol esters, lignin sulfite waste liquors or methylcellulose.

Powders, dusting and broadcasting agents can be prepared by mixing or milling the active substances together with a solid carrier.

Granules, for example coated, impregnated or homogeneous granules, can be prepared by binding the active ingredients to solid carriers such as mineral earths such as silica gel, silicic acids, silicates, talc, kaolin, limestone, lime, chalk, bole, loess, clay, dolomite, diatomaceous earth, calcium and magnesium sulfate, magnesium oxide, milled plastics, fertilizers such as ammonium sulfate, ammonium phosphate, ammonium nitrate and ureas and vegetable products such as cereal meal, bark meal, wood meal and nutshell meal, cellulose powder or other solid carriers.

The formulations contain from 0.1 to 95% by weight, preferably from 0.5 to 90% by weight, of active ingredient. The active ingredients are employed in a purity of from 90 to 100%, preferably 95% to 100% (according to the NMR spectrum).

The compounds I according to the invention can be formulated as follows, for example:

I. 90 parts by weight of compound No 40 are mixed with 10 parts by weight of N-methyl-α-pyrrolidone to give a solution which is suitable for application in the form of very small droplets.

II. 20 parts by weight of compound No. 40 are dissolved in a mixture composed of 80 parts by weight of xylene, 10 parts by weight of the adduct of 8 to 10 moles of ethylene oxide and 1 mole of oleic acid N-monoethanolamide, 5 parts by weight of calcium dodecylbenzenesulfonate and 5 parts by weight of the adduct of 40 moles of ethylene oxide and 1 mole of castor oil. Dispersing the solution in 100,000 parts by weight of water results in an aqueous dispersion which contains 0.02% by weight of the active ingredient.

III. 20 parts by weight of compound No. 40 are dissolved in a mixture composed of 40 parts by weight of cyclohexanone, 30 parts by weight of isobutanol, 20 parts by weight of the adduct of 7 moles of ethylene oxide and 1 mole of isooctylphenol and 10 parts by weight of the adduct of 40 moles of ethylene oxide and 1 mole of castor oil. Dispersing the solution in 100,000 parts by weight of water results in an aqueous dispersion containing 0.02% by weight of the active ingredient.

IV. 20 parts by weight of active ingredient No. 40 are dissolved in a mixture composed of 25 parts by weight of cyclohexanone, 65 parts by weight of a mineral oil fraction of boiling point 210° to 280° C. and 10 parts by weight of the adduct of 40 moles of ethylene oxide and 1 mole of castor oil. Dispersing the solution in 100,000 parts by weight of water results in an aqueous dispersion containing 0.02% by weight of the active ingredient.

V. 20 parts by weight of active ingredient No. 40 are thoroughly mixed with 3 parts by weight of sodium diisobutylnaphthylene-α-sulfonate, 17 parts by weight of the sodium salt of a ligninsulfonic acid from a sulfite waste liquor and 60 parts by weight of powdered silica gel and milled in a hammer mil. Dispersing the mixture in 20,000 parts by weight of water results in a spray liquor containing 0.1% by weight of the active ingredient.

VI. 3 parts by weight of active ingredient No. 40 are mixed with 97 parts by weight of finely divided kaolin. This results in a dusting agent containing 3% by weight of active ingredient.

VII. 30 parts by weight of active ingredient No. 40 are intimately mixed with a mixture of 92 parts by weight of powdered silica gel and 8 parts by weight of liquid paraffin which has been sprayed on to the surface of this silica gel. This results in a formulation of the active ingredient with good adhesion.

VIII. 20 parts by weight of active ingredient No. 40 are intimately mixed with 2 parts by weight of calcium dodecylbenzosulfonate, 8 parts by weight of fatty alcohol polyglycol ether, 2 parts by weight of the sodium salt of a phenol/urea/formaldehyde condensate and 68 parts by weight of a liquid paraffin.

This results in a stable oily dispersion.

The herbicidal and growth-regulating agents for the active ingredients can be applied in the pre-emergence or post-emergence process. If the active ingredients are less well tolerated by certain crop plants it is possible to employ application techniques in which the herbicides are spray on in such a way that the leaves of the sensitive crop plants are touched as little as possible while the active ingredients reach the leaves of unwanted plants growing thereunder or the uncovered surface of the soil (post-directed, lay-by).

The application rates of active ingredient when used as herbicides depend on the control to be achieved, the season, the target plants and the growth stage and are from 0.001 to 3, preferably 0.01 to 2 kg/ha active substance.

The compounds of the formula I are able to influence virtually all stages of development of a plant in various ways and are therefore employed as plant growth regulators. The variety of effects of the growth regulators depends, in particular,

a) on the species and variety of the plant,

b) on the time of application relative to the stage of development of the plant and to the season,

c) on the site and method of application (e.g. seed dressing, soil treatment, leaf application or trunk injection for trees)

d) on climatic factors, e.g. temperature, amount of precipitation, also on length of daylight and light intensity

e) on the soil characteristics (including fertilization),

f) on the formulation or application form of the active ingredient and, finally,

g) on the active substance concentrations used.

A few of the range of possible uses of the plant growth regulators of the formula I according to the invention in crop cultivation, in agriculture and horticulture are mentioned hereinafter.

A. The compounds according to the invention can be used to inhibit greatly the vegetative growth of the plants, which is evident, in particular, from a reduction in the height of growth. The treated plants accordingly exhibit stunted growth; there is also seen to be a darker color of the leaves.

It is advantageous in practice to reduce the vigor of grass growth on the edges of roads, hedgerows, canal banks and on grassed areas such as parks, sports grounds and orchards, lawns and airports to reduce the labor and cost of grass cutting.

Also of economic interest is the increase in the resistance to lodging of crops prone to this, such as cereals, corn, sunflowers and soybean. The shortening and strengthening of the stalk caused thereby reduces or eliminates the risk of lodging (bending over) of plants under unfavorable weather conditions before harvest.

Another important use of growth regulators is to reduce the height of growth and to alter the timing of ripening of cotton. This makes possible completely mechanized harvesting of this important crop plant.

The costs of pruning fruit and other trees can be saved by using the growth regulators. In addition, the alternation of fruit trees can be stopped by growth regulators.

Growth regulators can also be used to increase or inhibit the production of lateral branches by the plants. This is of interest when, for example, the production of side shoots (suckers) by tobacco plants is to be inhibited in favor of leaf growth.

Growth regulators can be used, for example, to increase considerably the frost resistance of winter rape. On the one hand, this reduces the height of growth and the development of an excessive (and thus particularly frost-susceptible) leaf or plant mass. On the other hand, the young rape plants are, after sowing and before onset of winter frosts, held back in the vegetative stage of development despite favorable growth conditions. This also eliminates the risk of frost on such plants which are prone to premature breakdown of flowering inhibition and to transition into the generative phase. It is also advantageous for other crops, e.g. winter cereals, to be treated with the compounds according to the invention in the fall and thus be well tillered but not too lush for the start of the winter. It is possible in this way to avert an increased sensitivity to frost and, because of the relatively low leaf and plant mass, attack by various diseases (e.g. fungal disease). The inhibition of vegetative growth additionally makes it possible with many crop plants to plant the soil more densely so that a higher yield per soil area can be achieved.

B. The growth regulators can be used to achieve higher yields both of plants parts and of plant constituents. Thus, for example, it is possible to induce the growth of larger amounts of buds, flowers, leaves, fruit, seed kernels, roots and tubers, to increase the content of sugar in sugar beet, sugar cane and citrus fruit, to raise the protein content in cereals or soybean or to stimulate rubber trees to an increased flow of latex.

In this connection, the compounds of the formula I can bring about increased yields by intervening in the plant metabolism or by promoting or inhibiting vegetative and/or generative growth.

C. Finally, plant growth regulators can be used to achieve both an increase or reduction in the length of stages of development and an increase or reduction in the rate of ripening of the harvested parts of the plants before or after the harvest.

Of economic interest is, for example, the facilitation of harvesting which is made possible by the concentration in time of the fall or reduced adhesion to the tree in the case of citrus fruit, olives or other species and varieties of pomes, drupes and caryopses. The same mechanism, i.e. the promotion of the development of separating tissue between the fruit and the leaf and shoot part of the plant is also essential for well-controlled defoliation of crop plants such as cotton.

D. Furthermore, growth-regulators can be used to reduce the water requirement of plants. This is particularly important for agricultural land which needs very costly artificial irrigation, e.g. in arid or semi-arid areas. Use of the substances according to the invention allows the intensity of irrigation to be reduced and thus improves the economics of farming. Growth regulators have the effect of improving utilization of the available water because, inter alia,

the width of opening of the stomata is reduced

a thicker epidermis and cuticula is formed

the spread of roots in the soil is improved and

the microclimate in the crop is beneficially affected by more compact growth.

The growth regulators of the formula I to be used according to the invention can be delivered to the crop plants both as seeds (as seed dressing) and via the soil, i.e. through the roots and, particularly preferably, through the leaf by spraying.

A wide variation in the application rate is possible because they are well tolerated by plants.

In view of the wide variety of application methods, the compounds according to the invention or the agents containing them can be used to eradicate unwanted plants in a large number of crops.

    ______________________________________                                         Crop list:                                                                     Botanical name        English name                                             ______________________________________                                         Allium cepa           cooking onion                                            Ananas comusus        pineapple                                                Arachis hypogaea      peanut                                                   Asparagus officinalis asparagus                                                Beta vulgaris spp. altissima                                                                         sugar beet                                               Beta vulgaris spp. rapa                                                                              fodder beet                                              Brassica napus var. napus                                                                            rape                                                     Brassica napus var. napobrassica                                                                     cabbage rape                                             Brassica rapa var. silvestris                                                                        turnip rape                                              Camellia sinensis     tea plant                                                Carthamus tinctorius  safflower                                                Carya illinoinensis   pecan nut                                                Citrus limon          lemon                                                    Citrus sinensis       orange                                                   Coffea arabica (Coffea canephora,                                                                    coffee                                                   Coffea liberica)                                                               Cucumis sativus       cucumber                                                 Cynodon dactylon      Bermuda grass                                            Daucus carota         carrot                                                   Elaeis guineensis     oil palm                                                 Fragaria vesca        strawberry                                               Glycine max           soybean                                                  Gossypium hirsutum (Gossypium                                                                        cotton                                                   aboreum, Gossypium herbaceum                                                   Gossypium vitifolium)                                                          Helianthus annuus     sunflower                                                Hevea brasiliensis    para rubber tree                                         Hordeum vulgare       barley                                                   Humulus lupulus       hops                                                     Ipomoea batatas       sweet potato                                             Juglans regia         walnut                                                   Lens culinaris        lentil                                                   Linum usitatissimum   flax                                                     Lycopersicon lycopersicum                                                                            tomato                                                   Malus spp.            apple                                                    Manihot esculenta     cassava                                                  Medicago sativa       alfalfa                                                  Musa spp.             bananas                                                  Nicotiana tabacum ( N. rustica)                                                                      tobacco                                                  Olea europaea         olive                                                    Oryza sativa          rice                                                     Phaseolus lunatus     lima bean                                                Phaseolus vulgaris    bush bean                                                Picea abies           spruce                                                   Pinus spp.            pine                                                     Pisum sativum         garden pea                                               Prunus avium          sweet cherry                                             Prunus persica        peach                                                    Pyrus communis        pear                                                     Ribes sylvestre       redcurrant                                               Ricinus communis      castor bean                                              Saccharum officinarum sugar cane                                               Secale cereale        rye                                                      Solanum tuberosum     potato                                                   Sorghum bicolor (S. vulgare)                                                                         millet                                                   Theobroma cacao       cocoa                                                    Trifolium pratense    red clover                                               Triticum aestivum     wheat                                                    Triticum durum        durum wheat                                              Vicia faba            horse bean                                               Vitis vinifera        grape vine                                               Zea mays              corn                                                     ______________________________________                                    

To extend the spectrum of action and to achieve synergistic effects, the compounds I according to the invention can be mixed and applied together with numerous representatives of other groups of herbicides or growth regulators. Examples of suitable mixing partners are diazine, 4H-3,1-benzoxazine derivatives, benzothiadiazinones, 2,6-dinitroanilines, N-phenylcarbamates, thiolcarbamates, halo carboxylic acids, triazines, amides, ureas, diphenyl ethers, triazinones, uracils, benzofuran derivatives, cyclohexane-1,3-dione derivatives, quinolinecarboxylic acid derivatives, sulfonylurea derivatives, aryloxy- and heteroaryloxyphenoxypropionic acids and the salts, esters and amides thereof, and others.

It may also be beneficial to apply the compounds I, alone or combined with other herbicides, mixed together with other crop protection agents, for example with pesticides, fungicides or bactericides. Also of interest is the possibility of mixing with mineral salt solutions which are employed to eliminate deficiencies in nutrients or trace elements. It is also possible to add non-phytotoxic oils and oil concentrates.

The examples which follow describe examples of the preparation of the compounds according to the invention.

EXAMPLE 1 N-(2-Methoxycarbonylphenylsulfonyl)-1,5-dimethylpyrazole-3-carboxamide

10.8 g of 2-methoxycarbonylphenylsulfonamide, 8.6 g of 1,5-dimethylpyrazole-3-carbonyl chloride and 13.8 g of potassium carbonate in 200 ml of absolute acetone are refluxed for 8 h. The solvent is removed by distillation and then the residue is taken up in water and the pH is adjusted to 2. The precipitate is filtered off with suction and washed with H₂ O until neutral. The residue is stirred with ether, filtered off with suction and dried under reduced pressure. 11.6 g of N-(2-methoxycarbonylphenylsulfonyl)-1,5-dimethylpyrazole-3-carboxamide with a melting point of 176°-177° C. are obtained (active ingredient Example No. 40).

EXAMPLE 2 N-(2-Thienylsulfonyl)-1-methylpyrazole-4-carboxamide

3.8 g of 1-methylpyrazole-4-carboxylic acid and 4.9 g of carbonyldiimidazole in 100 ml of 1,2-dichloroethane are heated at 55° C. for 3.5 h. 4.9 g of 2-thienylsulfonamide and 5.4 ml of triethylamine are added and then the mixture is heated at 55° C. for 13 h. After cooling, 40 ml of 10% strength aqueous NaOH solution are added and then the pH of the aqueous phase is adjusted to 1. The precipitate is removed and dried under reduced pressure. 5.2 g of N-(2-thienylsulfonyl)-1-methylpyrazole-4-carboxamide with a melting point of 174°-180° C. are obtained (active ingredient Example No. 103).

EXAMPLE 3 N-(2-Chlorophenylsulfonyl)-1,4-dimethylimidazole-2-carboxamide

2.0 g of 1,4-dimethylimidazole and 4.3 g of 2-chlorophenylsulfonyl isocyanate in 200 ml of toluene are refluxed for 6 h. The precipitate which forms on cooling is filtered off with suction and washed with acetone. The residue is suspended in acetonitrile/methanol and refluxed for 0.5 h. After cooling, the solid is filtered off with suction and dried under reduced pressure. 2.3 g of N-(2-chlorophenylsulfonyl)-1,4-dimethylimidazole-2-carboxamide with a melting point of 230°-231° C. are obtained. (Active ingredient Example No. 113).

EXAMPLE 4 N-(2,6-Dichlorophenylsulfonyl)-2-methoxythiazole-4-carboxamide

2.3 g of N-(2,6-dichlorophenylsulfonyl)-2-bromothiazole-4-carboxamide and 1.6 g of sodium methanolate in 45 ml of methanol are refluxed for 12 h. After cooling, the precipitate is filtered off with suction, washed with methanol and then dried under reduced pressure. 1.8 g of N-(2,6-dichlorophenylsulfonyl)-2-methoxythiazole-4-carboxamide with a melting point of 162°-165° C. are obtained. (Active ingredient Example No. 34).

The compounds which are listed in Table 1 which follows and in which the substituents A are as follows can be obtained correspondingly by appropriate choice of the starting materials and adjustment of the process conditions.

    ______________________________________                                         A1-1: R.sup.2 = CO.sub.2 CH.sub.3                                                                    R.sup.3, R.sup.4 = H                                     A1-2: R.sup.2 = CO.sub.2 CH.sub.2 CH.sub.3                                                           R.sup.3, R.sup.4 = H                                     A1-3: R.sup.2 = CO.sub.2 CH(CH.sub.3).sub.2                                                          R.sup.3, R.sup.4 = H                                     A1-4: R.sup.2 = CO.sub.2 CH.sub.3                                                                    R.sup.3 = 6-Cl,                                                                              R.sup.4 = H                                A1-5: R.sup.2 = CO.sub.2 CH.sub.3                                                                    R.sup.3 = 6-OCH.sub.3,                                                                       R.sup.4 = H                                A1-6: R.sup.2 = CO.sub.2 CH.sub.3                                                                    R.sup.3 = 6-CH.sub.3,                                                                        R.sup.4 = H                                A1-7: R.sup.2 = CO.sub.2 CH.sub.3                                                                    R.sup.3 = 6-F,                                                                               R.sup.4 = H                                A1-8: R.sup.2 = CO.sub.2 CH.sub.3                                                                    R.sup.3 = 3-Cl,                                                                              R.sup.4 = H                                A1-9: R.sup.2 = CO.sub.2 CH.sub.3                                                                    R.sup.3 = 3-F,                                                                               R.sup.4 = H                                A1-10:                                                                               R.sup.2 = CO.sub.2 CH.sub.3                                                                    R.sup.3 = 4-Cl,                                                                              R.sup.4 = H                                A1-11:                                                                               R.sup.2 = CO.sub.2 CH.sub.3                                                                    R.sup.3 = 5-Cl,                                                                              R.sup.4 = H                                A1-12:                                                                               R.sup.2 = CO.sub.2 CH.sub.3                                                                    R.sup.3 = 5-F,                                                                               R.sup.4 = H                                A1-13:                                                                               R.sup.2 = CO.sub.2 CH.sub.3                                                                    R.sup.3 = 5-OCH.sub.3,                                                                       R.sup.4 = H                                A1-14:                                                                               R.sup.2 = CO.sub.2 CH.sub.3                                                                    R.sup.3 = 5-OCHF.sub.2,                                                                      R.sup.4 = H                                A1-15:                                                                               R.sup.2 = CO N(CH.sub.3).sub.2                                                                 R.sup.3, R.sup.4 = H                                     A1-16:                                                                               R.sup.2 = CO N(CH.sub.3).sub.2                                                                 R.sup.3 = 3-Cl                                                                               R.sup.4 = H                                A1-17:                                                                               R.sup.2 = CO N(CH.sub.3).sub.2                                                                 R.sup.3 = 3-F R.sup.4 = H                                A1-18:                                                                               R.sup.2 = CH.sub.3                                                                             R.sup.3 = H,  R.sup.4 = H                                A1-19:                                                                               R.sup.2 = CH.sub.2 Cl                                                                          R.sup.3, R.sup.4 = H                                     A1-20:                                                                               R.sup.2 = CH.sub.2 OCH.sub.3                                                                   R.sup.3, R.sup.4 = H                                     A1-21:                                                                               R.sup.2 = CH.sub.2 SCH.sub.3                                                                   R.sup.3, R.sup.4 = H                                     A1-22:                                                                               R.sup.2 = CF.sub.3                                                                             R.sup.3, R.sup.4 = H                                     A1-23:                                                                               R.sup.2 = CH.sub.3                                                                             R.sup.3 = 5-Cl,                                                                              R.sup.4 = H                                A1-24:                                                                               R.sup.2 = CH.sub.3                                                                             R.sup.3 = 5-CH.sub.3,                                                                        R.sup.4 = H                                A1-25:                                                                               R.sup.2 = CH.sub.3                                                                             R.sup.3 = 5-OCH.sub.3,                                                                       R.sup.4 = H                                A1-26:                                                                               R.sup.2 = F     R.sup.3, R.sup.4 = H                                     A1-27:                                                                               R.sup.2 = F     R.sup.3 = 6-F,                                                                               R.sup.4 = H                                A1-28:                                                                               R.sup.2 = Cl    R.sup.3, R.sup.4 = H                                     A1-29:                                                                               R.sup.2 = Cl    R.sup. 3 = 6-Cl,                                                                             R.sup.4 = H                                A1-30:                                                                               R.sup.2 = Cl    R.sup.3 = 6-CH.sub.3,                                                                        R.sup.4 = H                                A1-31:                                                                               R.sup.2 = Cl    R.sup.3 = 6-OCH.sub.3,                                                                       R.sup.4 = H                                A1-32:                                                                               R.sup.2 = Cl    R.sup.3 = 5-CO.sub.2 CH.sub.3,                                                               R.sup.4 = H                                A1-33:                                                                               R.sup.2 = Cl    R.sup.3 = 5-Cl,                                                                              R.sup.4 = H                                A1-34:                                                                               R.sup.2 = Cl    R.sup.3 = 3-Cl,                                                                              R.sup.4 = H                                A1-35:                                                                               R.sup.2 = Cl    R.sup.3 = 6-Cl,                                                                              R.sup.4 =                                                                      5-Cl                                       A1-36:                                                                               R.sup.2 = Cl    R.sup.3 = 6-Cl,                                                                              R.sup.4 =                                                                      4-Cl                                       A1-37:                                                                               R.sup.2 = Br    R.sup.3, R.sup.4 = H                                     A1-38:                                                                               R.sup.2 = Br    R.sup.3 = 6-Br,                                                                              R.sup.4 = H                                A1-39:                                                                               R.sup.2 = CN    R.sup.3, R.sup.4 = H                                     A1-40:                                                                               R.sup.2 = OCH.sub.3                                                                            R.sup.3, R.sup.4 = H                                     A1-41:                                                                               R.sup.2 = OCH.sub.2 CH.sub.3                                                                   R.sup.3, R.sup.4 = H                                     A1-42:                                                                               R.sup.2 = OCH(CH.sub.3).sub.2                                                                  R.sup.3, R.sup.4 = H                                     A1-43:                                                                               R.sup.2 = OCH.sub.2 CH.sub.2 Cl                                                                R.sup.3, R.sup.4 = H                                     A1-44:                                                                               R.sup.2 = CH.sub.2 CH.sub.2 OCH.sub.3                                                          R.sup.3, R.sup.4 = H                                     A1-45:                                                                               R.sup.2 = OCH.sub.2 CF.sub.3                                                                   R.sup.3, R.sup.4 = H                                     A1-46:                                                                               R.sup.2 = OCF.sub.3                                                                            R.sup.3, R.sup.4 = H                                     A1-47:                                                                               R.sup.2 = OCF.sub.2 H                                                                          R.sup.3, R.sup.4 = H                                     A1-48:                                                                               R.sup.2 = OCH.sub.3                                                                            R.sup.3 = 5-Br,                                                                              R.sup.4 = H                                A1-49:                                                                               R.sup.2 = OCH.sub.3                                                                            R.sup.3 = 5-OCH.sub.3,                                                                       R.sup.4 =  H                               A1-50:                                                                               R.sup.2 = OCH.sub.2 CF.sub.3                                                                   R.sup.3 = 5-OCH.sub.2 CF.sub.3,                                                              R.sup.4 = H                                A1-51:                                                                               R.sup.2 = SCH.sub.3                                                                            R.sup.3, R.sup.4 = H                                     A1-52:                                                                               R.sup.2 = SCH.sub.2 CH.sub.3                                                                   R.sup.3, R.sup.4 = H                                     A1-53:                                                                               R.sup.2 = SO.sub.2 CH.sub.3                                                                    R.sup.3, R.sup.4 = H                                     A1-54:                                                                               R.sup.2 = SO.sub.2 CH.sub.2 CH.sub.3                                                           R.sup.3, R.sup.4 = H                                     A1-55:                                                                               R.sup.2 = SO.sub.2 CH.sub.2 CH.sub.2 CH.sub.3                                                  R.sup.3, R.sup.4 = H                                     A1-56:                                                                               R.sup.2 = SO.sub.2 CH(CH.sub.3).sub.2                                                          R.sup.3, R.sup.4 = H                                     A1-57:                                                                               R.sup.2 = SO.sub.2 N(CH.sub.3).sub.2                                                           R.sup.3, R.sup.4 = H                                     A1-58:                                                                               R.sup.2 = OSO.sub.2 CH.sub.3                                                                   R.sup.3, R.sup.4 = H                                     A1-59:                                                                               R.sup.2 = OSO.sub.2 CH.sub.2 CH.sub.3                                                          R.sup. 3, R.sup.4 = H                                    A1-60:                                                                               R.sup.2 = COCH.sub.3                                                                           R.sup.3, R.sup.4 = H                                     A1-61:                                                                                ##STR12##      R.sup.3, R.sup.4 = H                                     A2-1: R.sup.5 = H     R.sup.6 = H                                              A2-2: R.sup.5 = CO.sub.2 CH.sub.3                                                                    R.sup.6 = H                                              A2-3: R.sup.5 = CO.sub.2 CH.sub.2 CH.sub.3                                                           R.sup.6 = H                                              A2-4: R.sup.5 = CON(CH.sub.3).sub.2                                                                  R.sup.6 = H                                              A2-5: R.sup.5 = Cl    R.sup.6 = H                                              A2-6: R.sup.5 = CF.sub.3                                                                             R.sup.6 = H                                              A2-7: R.sup.5 = OCH.sub.2 CH.sub.3                                                                   R.sup.6 = H                                              A2-8: R.sup.5 = SO.sub.2 CH.sub.3                                                                    R.sup.6 = H                                              A2-9: R.sup.5 = SO.sub.2 CH.sub.2 CH.sub.3                                                           R.sup.6 = H                                              A3-1: R.sup.5 = H     R.sup.6 = H                                              A3-2: R.sup.5 = CON(CH.sub.3).sub.2                                                                  R.sup.6 = H                                              A6-1: R.sup.5 = H     R.sup.4 = H   X = S                                      A6-2: R.sup.5 = Cl    R.sup.4 = H   X = S                                      A6-3: R.sup.5 = H     R.sup.4 = 4-Cl                                                                               X = S                                      A6-4: R.sup.5 = H     R.sup.4 = 5-Cl                                                                               X = S                                      A6-5: R.sup.5 = CO.sub.2 CH.sub.3                                                                    R.sup.4 = H   X = S                                      A7-1: R.sup.6 = H     R.sup.7 = CO.sub.2 CH.sub.3                                                                  X = S                                      A7-2: R.sup.6 = H     R.sup.7 = CON(CH.sub.3).sub.2                                                                X = S                                      A8-1: R.sup.6 = H     R.sup.7 = CO.sub.2 CH.sub.3                                                                  X = S                                      A9-1: R.sup.5 = H     R.sup.4 = H                                              A9-2: R.sup.5 = 2-CO.sub.2 CH.sub.3                                                                  R.sup.4 = H                                              A9-3: R.sup.5 = 2-Cl  R.sup.4 = H                                              A9-4: R.sup.5 = 8-CO.sub.2 CH.sub.3                                                                  R.sup.4 = H                                              A9-5: R.sup.5 = 8-Cl  R.sup.4 = H                                              A9-6: R.sup.5 = 8-OCH.sub.3                                                                          R.sup.4 = H                                              A9-7: R.sup.5 = 8-OCH.sub.2 CH.sub.2 OCH.sub.3                                                       R.sup.4 = H                                              A9-8: R.sup.5 = 8-OCH.sub.2 CH.sub.2 Cl                                                              R.sup.4 = H                                              A10-1:                                                                               R.sup.5 = H     R.sup.4 = H                                              A10-2:                                                                               R.sup.5 = 1-CO.sub.2 CH.sub.3                                                                  R.sup.4 = H                                              A10-3:                                                                               R.sup.5 = 1-Cl  R.sup.4 = H                                              A10-4:                                                                               R.sup.5 = 1-OCH.sub.2 CH.sub.2 OCH.sub.3                                                       R.sup.4 = H                                              A10-5:                                                                               R.sup.5 = 1-OCH.sub.2 CH.sub.2 Cl                                                              R.sup.4 = H                                              ______________________________________                                    

                  TABLE 1                                                          ______________________________________                                          ##STR13##                                                                     No.  A       B                     M.p. (°C.)                           ______________________________________                                          1   A1-1    2-furyl                                                            2   A1-26   2-furyl               158-160                                      3   A1-29   2-furyl                                                            4   A1-1    2,5-dimethyl-3-furyl  148-150                                      5   A1-11   2,5-dimethyl-3-furyl                                               6   A1-1    5-nitro-2-furyl                                                    7   A6-1    5-nitro-2-furyl                                                    8   A1-40   5-chloro-2-thienyl    175-177                                      9   A1-1    5-chloro-2-thienyl                                                10   A1-1    5-methyl-2-thienyl    180-181                                     11   A1-18   5-methyl-2-thienyl                                                12   A1-1    2-pyrrolyl            220                                         13   A1-29   2-pyrrolyl            210                                         14   A1-1    1-methyl-2-pyrrolyl   162-164                                     15   A1-28   1-methyl-2-pyrrolyl                                               16   A1-1    3-isoxazolyl                                                      17   A1-26   3-isoxazolyl          170-171                                     18   A1-29   5-methyl-3-isoxazolyl 138                                         19   A1-1    5-methyl-3-isoxazolyl                                             20   A1-1    5-chloromethyl-3-isoxazolyl                                       21   A1-40   5-chloromethyl-3-isoxazolyl                                       22   A1-30   5-phenyl-3-isoxazolyl 200-202                                     23   A1-1    3-methyl-4-isoxazolyl 142-143                                     24   A1-1    3,5-dimethyl-4-isoxazolyl                                         25   A1-28   3,5-dimethyl-4-isoxazolyl                                         26   A1-1    5-isoxazolyl                                                      27   A1-27   5-isoxazolyl                                                      28   A1-1    3-methyl-5-isoxazolyl 123-127                                     29   A1-30   3-methyl-5-isoxazolyl 137-139                                     30   A1-1    2-bromo-4-thiazolyl                                               31   A1-29   2-bromo-4-thiazolyl   >230                                        32   Al-30   2-bromo-4-thiazolyl   151                                         33   A1-1    2-methoxy-4-thiazolyl                                             34   A1-29   2-methoxy-4-thiazolyl 162-165                                     35   A1-30   2-methoxy-4-thiazolyl 138                                         36   A1-1    2-methyl-4-thiazolyl                                              37   A1-29   2-methyl-4-thiazolyl                                              38   A1-1    4-methyl-2-thiazolyl                                              39   A1-30   4-methyl-2-thiazolyl                                              40   A1-1    1,5-dimethyl-3-pyrazolyl                                                                             176-177                                     41   A1-29   1,5-dimethyl-3-pyrazolyl                                                                             135-138                                     42   A1-30   1,5-dimethyl-3-pyrazolyl                                                                             123                                         43   A1-28   1,5-dimethyl-3-pyrazolyl                                                                             89-91                                       44   A1-40   1,4-dimethyl-3-pyrazolyl                                                                             123                                         45   A1-18   1,5-dimethyl-3-pyrazolyl                                                                             144-145                                     46   A1-27   1,5-dimethyl-3-pyrazolyl                                                                             145-147                                     47   A1-33   1,5-dimethyl-3-pyrazolyl                                                                             172-178                                     48   A1-11   1,5-dimethyl-3-pyrazolyl                                                                             172-174                                     49   A1-10   1,5-dimethyl-3-pyrazolyl                                                                             166-169                                     50   A1-9    1,5-dimethyl-3-pyrazolyl                                                                             168-169                                     51   A1-2    1,5-dimethyl-3-pyrazolyl                                                                             124-125                                     52   A1-3    1,5-dimethyl-3-pyrazolyl                                          53   A1-15   1,5-dimethyl-3-pyrazolyl                                                                             201-203                                     54   A2-9    1,5-dimethyl-3-pyrazolyl                                                                             185-188                                     55   A7-1    1,5-dimethyl-3-pyrazolyl                                                                             140-142                                     56   A9-1    1,5-dimethyl-3-pyrazolyl                                                                             125-128                                     57   A1-1    4-bromo-1,5-dimethyl-3-pyrazolyl                                                                     204-205                                     58   A1-28   4-bromo-1,5-dimethyl-3-pyrazolyl                                                                     200-201                                     59   A1-26   4-bromo-1,5-dimethyl-3-pyrazolyl                                                                     194-195                                     60   A1-30   4-bromo-1,5-dimethyl-3-pyrazolyl                                                                     205-206                                     61   A1-29   4-bromo-1,5-dimethyl-3-pyrazolyl                                                                     210                                         62   A1-27   4-bromo-1,5-dimethyl-3-pyrazolyl                                                                     192-193                                     63   A1-9    4-bromo-1,5-dimethyl-3-pyrazolyl                                                                     192-193                                     64   A1-2    4-bromo-1,5-dimethyl-3-pyrazolyl                                                                     180-182                                     65   A1-3    4-bromo-1,5-dimethyl-3-pyrazolyl                                  66   A2-9    4-bromo-1,5-dimethyl-3-pyrazolyl                                  67   A1-1    4-chloro-1,5-dimethyl-3-pyrazolyl                                                                    192-194                                     68   A1-11   4-chloro-1,5-dimethyl-3-pyrazolyl                                                                    196-197                                     69   A1-29   4-chloro-1,5-dimethyl-3-pyrazolyl                                                                    210                                         70   A1-30   4-chloro-1,5-dimethyl-3-pyrazolyl                                                                    194-195                                     71   A1-40   4-chloro-1,5-dimethyl-3-pyrazolyl                                                                    201-204                                     72   A1-1    1,4-dimethyl-3-pyrazolyl                                          73   A1-2    1,4-dimethyl-3-pyrazolyl                                          74   A1-28   1,4-dimethyl-3-pyrazolyl                                          75   A1-27   1,4-dimethyl-3-pyrazolyl                                          76   A1-30   1,4-dimethyl-3-pyrazolyl                                          77   A1-1    1,4,5-trimethyl-3-pyrazolyl                                                                          184-186                                     78   A1-29   1,4,5-trimethyl-3-pyrazolyl                                                                          145-146                                     79   A1-40   1,4,5-trimethyl-3-pyrazolyl                                       80   A1-1    4-ethoxycarbonyl-1-methyl-3-pyrazoyl                                                                 162-164                                     81   A1-30   4-ethoxycarbonyl-1-methyl-3-pyrazoyl                                                                 197-200                                     82   A1-1    1-ethyl-5-methyl-3-pyrazolyl                                                                         35-37                                       83   A1-11   1-ethyl-5-methyl-3-pyrazolyl                                                                         62-63                                       84   A1-27   1-ethyl-5-methyl-3-pyrazolyl                                      85   A1-43   1-ethyl-5-methyl-3-pyrazolyl                                      86   A1-29   1-ethyl-5-methyl-3-pyrazolyl                                                                         171-173                                     87   A1-1    1-isopropyl-5-methyl-3-pyrazolyl                                                                     156-158                                     88   A1-29   1-isopropyl-5-methyl-3-pyrazolyl                                                                     206-208                                     89   A1-40   1-isopropyl-5-methyl-3-pyrazolyl                                  90   A1-1    1-methyl-1,4,5,6-tetrahydrocyclo-                                                                    187-188                                                  pentapyrazol-3-yl                                                 91   A1-28   1-methyl-1,4,5,6-tetrahydrocyclo-                                              pentapyrazol-3-yl                                                 92   A1-30   1-methyl-1,4,5,6-tetrahydrocyclo-                                              pentapyrazol-3-yl                                                 93   A1-40   1-methyl-1,4,5,6-tetrahydrocyclo-                                              pentapyrazol-3-yl                                                 94   A1-1    1-methyl-4,5,6,7-tetrahydrobenzo                                                                     157-158                                                  pyrazol-3-yl                                                      95   A1-26   1-methyl-4,5,6,7-tetrahydro                                                                          134-135                                                  benzopyrazol-3-yl                                                 96   A1-43   1-methyl-4,5,6,7-tetrahydro                                                    benzopyrazol-3-yl                                                 97   A1-2    1-methyl-4,5,6,7-tetrahydro                                                    benzopyrazol-3-yl                                                 98   A1-1    1,3-dimethyl-5-pyrazolyl                                                                             158-162                                     99   A1-30   1,3-dimethyl-5-pyrazolyl                                                                             203                                         100  A1-29   1,3-dimethyl-5-pyrazolyl                                                                             >230                                        101  A1-1    1-methyl-4-pyrazolyl  174-178                                     102  A1-30   1-methyl-4-pyrazolyl  208                                         103  A6-1    1-methyl-4-pyrazolyl  174-180                                     104  A9-1    1-methyl-4-pyrazolyl  220-227                                     105  A1-1    5-cyclopropyl-1-methyl-3-pyrazolyl                                                                   150-152                                     106  A1-27   5-cyclopropyl-1-methyl-3-pyrazolyl                                107  A1-30   5-cyclopropyl-1-methyl-3-pyrazolyl                                                                   148-150                                     108  A1-40   5-cyclopropyl-1-methyl-3-pyrazolyl                                109  A1-1    5-ethyl-1-methyl-3-pyrazolyl                                      110  A1-15   5-ethyl-1-methyl-3-pyrazolyl                                      111  A1-30   5-ethyl-1-methyl-3-pyrazolyl                                      112  A1-43   5-ethyl-1-methyl-3-pyrazolyl                                      113  A1-28   1,4-dimethyl-2-imidazolyl                                                                            230-231                                     114  A1-1    1,4-dimethyl-2-imidazolyl                                         115  A1-28   1-methyl-2-imidazolyl 162-165                                     116  A1-1    1-methyl-2-imidazolyl                                             117  A1-29   1-methyl-2-imidazolyl                                             118  A1-1    1-methyl-5-imidazolyl 220                                         119  A1-26   1-methyl-5-imidazolyl, Na salt                                                                       >300                                        120  A1-30   1-methyl-5-imidazolyl 255                                         121  A1-30   1-methyl-5-imidazolyl Na salt                                                                        >300                                        122  A1-40   1-methyl-5-imidazolyl 260-265                                     123  A1-29   1-methyl-5-imidazolyl 295-300                                     124  A1-1    2-methyl-4-oxazolyl                                               125  A1-26   2-methyl-4-oxazolyl                                               126  A1-30   2-methyl-4-oxazolyl                                               127  A1-44   2-methyl-4-oxazolyl                                               128  A1-1    2-cyclopropyl-4-oxazolyl                                                                             110-112                                     129  A1-2    2-cyclopropyl-4-oxazolyl                                          130  A1-27   2-cyclopropyl-4-oxazolyl                                                                             164-166                                     131  A9-1    2-cyclopropyl-4-oxazolyl                                          132  A1-1    1,2,3-thiadiazolyl-4-yl                                                                              110                                         133  A1-28   1,2,3-thiadiazolyl-4-yl                                                                              173-176                                     134  A1-29   1,2,3-thiadiazolyl-4-yl                                                                              >230                                        135  A1-33   1,2,3-thiadiazolyl-4-yl                                                                              139                                         136  A1-1    4-methyl-1,2,3-thiadiazolyl-5-yl                                  137  A1-28   4-methyl-1,2,3-thiadiazol-5-yl                                    138  A1-27   4-chloro-1,5-dimethyl-3-pyrazolyl                                                                    198-200                                     139  A1-1    5-phenyl-3-isoxazolyl 205-206                                     140  A1-11   4-bromo-1,5-dimethyl-3-pyrazolyl                                                                     >210                                        141  A1-26   1,5-dimethyl-3-pyrazolyl                                                                             146-147                                     142  A1-22   1,5-dimethyl-3-pyrazolyl                                                                             152-153                                     143  A1-28   5-methyl-3-isoxazolyl 190-191                                     144  A2-4    1,5-dimethyl-3-pyrazolyl                                                                             191-192                                     145  A1-49   1,5-dimethyl-3-pyrazolyl                                                                             153-155                                     146  A1-1    1,5-dimethyl-3-pyrazolyl, Na salt                                                                    >220                                        147  A1-1    1,5-dimethyl-3-pyrazolyl, Ca salt                                                                    >220                                        148  A1-11   1-methyl-1,4,5,6-tetrahydrocyclo-                                                                    184-187                                                  pentapyrazol-3-yl                                                 149  A1-27   5-methyl-3-isoxazolyl 160-161                                     150  A1-22   5-methyl-3-isoxazolyl 160-162                                     151  A1-10   2-cyclopropyl-4-oxazolyl                                                                             150-152                                     152  A1-30   2-cyclopropyl-4-oxazolyl                                                                             131-132                                     153  A1-22   2-cyclopropyl-4-oxazolyl                                                                             129-131                                     154  A1-44   1,5-dimethyl-3-pyrazolyl                                                                             83-85                                       155  A6-1    1,5-dimethyl-3-pyrazolyl                                                                             130-132                                     156  A1-9    5-cyclopropyl-1-methyl-3-pyrazolyl                                                                   100-101                                     157  A1-10   4-chloro-1,5-dimethyl-3-pyrazolyl                                                                    210-212                                     158  A1-9    4-chloro-1,5-dimethyl-3-pyrazolyl                                                                    194-195                                     159  A2-4    4-bromo-1,5-dimethyl-3-pyrazolyl                                                                     199                                         160  A1-22   4-bromo-1,5-dimethyl-3-pyrazolyl                                                                     175-177                                     161  A1-18   4-bromo-1,5-dimethyl-3-pyrazolyl                                                                     155-157                                     162  A1-1    1,4,5-trimethyl-3-pyrazolyl, Na salt                                                                 >220                                        163  A1-30   1,4,5-trimethyl-3-pyrazolyl                                                                          148-150                                     164  A1-1    4,5-diethyl-1-methyl-3-pyrazolyl                                                                     154-156                                     165  A1-1    4,5-diethyl-1-methyl-3-pyrazolyl,                                                                    90-92                                                    Na salt                                                           166  A1-2    4,5-diethyl-1-methyl-3-pyrazolyl                                                                     137-139                                     167  A1-2    4,5-diethyl-1-methyl-3-pyrazolyl,                                                                    157-159                                                  Na salt                                                           168  A1-9    4,5-diethyl-1-methyl-3-pyrazolyl                                                                     167-169                                     169  A1-9    4,5-diethyl-1-methyl-3-pyrazolyl,                                                                    130-132                                                  Na salt                                                           170  A1-10   4,5-diethyl-1-methyl-3-pyrazolyl                                                                     116-118                                     171  A2-4    4,5-diethyl-1-methyl-3-pyrazolyl                                                                     121-123                                     172  A1-29   4,5-diethyl-1-methyl-3-pyrazolyl                                                                     128-130                                     173  A1-29   4,5-diethyl-1-methyl-3-pyrazolyl                                                                     141-143                                                  Na salt                                                           174  A1-27   4,5-diethyl-1-methyl-3-pyrazolyl,                                                                    >220                                                     Na salt                                                           175  A1-30   4,5-diethyl-1-methyl-3-pyrazolyl                                                                     96-98                                       176  A1-30   4,5-diethyl-1-methyl-3-pyrazolyl,                                                                    >220                                                     Na salt                                                           177  A1-22   4,5-diethyl-1-methyl-3-pyrazolyl                                                                     93-95                                       178  A1-22   4,5-diethyl-1-methyl-3-pyrazolyl,                                                                    82-84                                                    Na salt                                                           179  A1-28   4,5-diethyl-1-methyl-3-pyrazolyl                                                                     150-152                                     180  A1-28   4,5-diethyl-1-methyl-3-pyrazolyl,                                                                    120-122                                                  Na salt                                                           181  A1-9    1-methyl-4,5,6,7-tetrahydro-                                                                         177-178                                                  benzopyrazol-3-yl                                                 182  A1-10   1-methyl-4,5,6,7-tetrahydro-                                                                         180-181                                                  benzopyrazol-3-yl                                                 183  A1-29   1-methyl-4,5,6,7-tetrahydro-                                                                         210                                                      benzopyrazol-3-yl                                                 184  A1-30   1-methyl-4,5,6,7-tetrahydro-                                                                         167-168                                                  benzopyrazol-3-yl                                                 185  A1-27   1-methyl-4,5,6,7-tetrahydro-                                                                         161-162                                                  benzopyrazol-3-yl                                                 186  A1-28   1-methyl-4,5,6,7-tetrahydro-                                                                         125-126                                                  benzopyrazol-3-yl                                                 187  A1-1    1-ethyl-5-methyl-3-pyrazolyl, Na salt                                                                168-170                                     188  A1-2    1-ethyl-5-methyl-3-pyrazolyl                                                                         90-92                                       189  A1-30   1-ethyl-5-methyl-3-pyrazolyl                                                                         120-121                                     190  A1-28   1-ethyl-5-methyl-3-pyrazolyl                                                                         133-135                                     191  A1-1    1-methyl-3-phenyl-4-pyrazolyl                                                                        32-34                                       192  A1-30   1-methyl-5-phenyl-4-pyrazolyl                                                                        199-201                                     ______________________________________                                    

It is also possible in a similar way to prepare further compounds of the structure ##STR14## where A can be a radical from the group E1 to E97

B can be a radical from the group G1 to G12

X can be O, S or NR⁹

W can be O or S

R⁸ can be a radical from the group L1 to L140

R⁹ can be a radical from the group V1 to V35 for example, and any combination of E, G, L, V, W and X is possible,

or where

A can be a radical from the group E1 to E97

B can be a radical from the group G13 to G14

X can be O or S

W can be O or S

R⁸ can be a radical from the group L1 to L140 for example, and any combination of E, G, L, W and X is possible,

or where

A can be a radical from the group E1 to E97

B can be the radical G15

X can be N

W can be O or S

R¹⁰ can be a radical from the group Y1 to Y16

R¹¹ can be a radical from the group Z1 to Z13 for example, and any combination of E, G, W, Y and Z is possible

Examples of possible meanings of A, B, R⁸, R⁹, R¹⁰ and R¹¹ are the following:

    ______________________________________                                         Comp. No.                                                                      ______________________________________                                                     A                                                                  E1          2-CO.sub.2 CH.sub.3C.sub.6 H.sub.4                                 E2          2-CO.sub.2 CH.sub.2 CH.sub.3C.sub.6 H.sub.4                        E3          2-CO.sub.2 CH(CH.sub.3).sub.2C.sub.6 H.sub.4                       E4          2-CO.sub.2 CH.sub.3 -6-ClC.sub.6 H.sub.3                           E5          2-CO.sub.2 CH.sub.3 -6-OCH.sub.3C.sub.6 H.sub.3                    E6          2-CO.sub.2 CH.sub.3 -6-CH.sub.3C.sub.6 H.sub.3                     E7          2-CO.sub.2 CH.sub.3 -3-ClC.sub.6 H.sub.3                           E8          2-CO.sub.2 CH.sub.3 -3-FC.sub.6 H.sub.3                            E9          2-CO.sub.2 CH.sub.3 -6-FC.sub.6 H.sub.3                            E10         2-CO.sub.2 CH.sub.3 -4-ClC.sub.6 H.sub.3                           E11         2-CO.sub.2 CH.sub.3 -5-ClC.sub.6 H.sub.3                           E12         2-CO.sub.2 CH.sub.3 -5-FC.sub.6 H.sub.3                            E13         2-CO.sub.2 CH.sub.3 -5-OCH.sub.3C.sub.6 H.sub.3                    E14         2-CO.sub.2 CH.sub.3 -5-OCHF.sub.2C.sub.6 H.sub.3                   E15         2-CON(CH.sub.3).sub.2C.sub.6 H.sub.4                               E16         2-CON(CH.sub.3).sub.2 -3-ClC.sub.6 H.sub.3                         E17         2-CON(CH.sub.3).sub.2 -3-FC.sub.6 H.sub.3                          E18         2-CH.sub.3C.sub.6 H.sub.4                                          E19         2-CH.sub.2 ClC.sub.6 H.sub.4                                       E20         2-CH.sub.2 OCH.sub.3C.sub.6 H.sub.4                                E21         2-CH.sub.2 SCH.sub.3C.sub.6 H.sub.4                                E22         2-CF.sub.3C.sub.6 H.sub.4                                          E23         2-CH.sub.3 -5-ClC.sub.6 H.sub.3                                    E24         2,5-(CH.sub.3).sub.2C.sub.6 H.sub.3                                E25         2-CH.sub.3 -5-OCH.sub.3C.sub.6 H.sub.3                             E26         2-FC.sub.6 H.sub.4                                                 E27         2,6-F.sub.2C.sub.6 H.sub.3                                         E28         2-ClC.sub.6 H.sub.4                                                E29         2,6-Cl.sub.2C.sub.6 H.sub.3                                        E30         2-Cl-6-CH.sub.3C.sub.6 H.sub.3                                     E31         2-Cl-6-OCH.sub.3C.sub.6 H.sub.3                                    E32         2-Cl-5-CO.sub.2 CH.sub.3C.sub.6 H.sub.3                            E33         2,5-Cl.sub.2C.sub.6 H.sub.3                                        E34         2,3-Cl.sub.2C.sub.6 H.sub.3                                        E35         2,5,6-Cl.sub.3C.sub.6 H.sub.2                                      E36         2,4,6-Cl.sub.3C.sub.6 H.sub.2                                      E37         2-BrC.sub.6 H.sub.4                                                E38         2,6-Br.sub.2C.sub.6 H.sub.3                                        E39         2-CNC.sub.6 H.sub.4                                                E40         2-OCH.sub.3C.sub.6 H.sub.4                                         E41         2-OCH.sub.2 CH.sub.3C.sub.6 H.sub.4                                E42         2-OCH(CH.sub.3).sub.2C.sub.6 H.sub.4                               E43         2-OCH.sub.2 CH.sub.2 ClC.sub.6 H.sub.4                             E44         2-OCH.sub.2 CH.sub.2 OCH.sub.3C.sub.6 H.sub.4                      E45         2-OCH.sub.2 CF.sub.3                                               E46         2-OCF.sub. 3                                                       E47         2-OCF.sub.2 HC.sub.6 H.sub.4                                       E48         2-OCH.sub.3 -5-BrC.sub.6 H.sub.3                                   E49         2,5-(OCH.sub.3).sub.2C.sub.6 H.sub.3                               E50         2,5-(OCH.sub.2 CF.sub.3).sub.2C.sub.6 H.sub.3                      E51         2-SCH.sub.3C.sub.6 H.sub.4                                         E52         2-SCH.sub.2 CH.sub.3C.sub.6 H.sub.4                                E53         2-SO.sub.2 CH.sub.3C.sub.6 H.sub.4                                 E54         2-SO.sub.2 CH.sub.2 CH.sub.3C.sub.6 H.sub.4                        E55         2-SO.sub.2 CH.sub.2 CH.sub.2 CH.sub.3C.sub.6 H.sub.4               E56         2-SO.sub.2 CH(CH.sub.3).sub.2C.sub.6 H.sub.4                       E57         2-SO.sub.2 N(CH.sub.3).sub.2C.sub.6 H.sub.4                        E58         2-OSO.sub.2 CH.sub.3C.sub.6 H.sub.4                                E59         2-OSO.sub.2 CH.sub.2 CH.sub.3C.sub.6 H.sub.4                       E60         2-COCH.sub.3C.sub.6 H.sub.4                                        E61         2-C.sub.6 H.sub.5C.sub.6 H.sub.4                                   E62         Pyrid-2-yl                                                         E63         3-CO.sub.2 CH.sub.3 -pyrid-2-yl                                    E64         3-CO.sub.2 CH.sub.2 CH.sub.3 -pyrid-2-yl                           E65         3-CON(CH.sub.3).sub.2 -pyrid-2-yl                                  E66         3-Cl-pyrid-2-yl                                                    E67         3-CF.sub.3 -pyrid-2-yl                                             E68         3-OCH.sub.2 CH.sub.3 -pyrid-2-yl                                   E69         3-SO.sub.2 CH.sub.3 -pyrid-2-yl                                    E70         3-SO.sub.2 CH.sub.2 CH.sub.3 -pyrid-2-yl                           E71         3-SOCH.sub.3 -pyrid-2-yl                                           E72         3-SOC.sub.2 H.sub. 5 -pyrid-2-yl                                   E73         3-SO.sub.2 N(CH.sub.3).sub.2 -pyrid-2-yl                           E74         3-SO.sub.2 NHCH(CH.sub.3).sub.2 -pyrid-2-yl                        E75         Pyrid-3-yl                                                         E76         2-CON(CH.sub.3).sub.2 -pyrid-3-yl                                  E77         Thien-2-yl                                                         E78         3-Cl-thien-2-yl                                                    E79         4-Cl-thien-2-yl                                                    E80         5-Cl-thien-2-yl                                                    E81         3-CO.sub.2 CH.sub.3 -thien-2-yl                                    E82         2-CO.sub.2 CH.sub.3 -thien-3-yl                                    E83         2-CON(CH.sub.3).sub.2 -thien-3-yl                                  E84         4-CO.sub.2 CH.sub.3 -thien-3-yl                                    E85         Naphth-1-yl                                                        E86         2-CO.sub.2 CH.sub.3 -naphth-1-yl                                   E87         2-Cl-naphth-1-yl                                                   E88         8-CO.sub.2 CH.sub.3 -naphth-1-yl                                   E89         8-Cl-naphth-1-yl                                                   E90         8-OCH.sub.3 -naphth-1-yl                                           E91         8-OCH.sub.2 CH.sub.2 OCH.sub.3 -naphth-1-yl                        E92         8-OCH.sub.2 CH.sub.2 Cl-naphth-1-yl                                E93         Naphth-2-yl                                                        E94         1-CO.sub.2 CH.sub.3 -naphth-2-yl                                   E95         1-Cl-naphth-2-yl                                                   E96         1-OCH.sub.2 CH.sub.2 OCH.sub.3 -naphth-2-yl                        E97         1-OCH.sub.2 CH.sub.2 Cl-naphth-2-yl                                            B                                                                  G1                                                                                          ##STR15##                                                         G2                                                                                          ##STR16##                                                         G3                                                                                          ##STR17##                                                         G4                                                                                          ##STR18##                                                         G5                                                                                          ##STR19##                                                         G6                                                                                          ##STR20##                                                         G7                                                                                          ##STR21##                                                         G8                                                                                          ##STR22##                                                         G9                                                                                          ##STR23##                                                         G10                                                                                         ##STR24##                                                         G11                                                                                         ##STR25##                                                         G12                                                                                         ##STR26##                                                         G13                                                                                         ##STR27##                                                         G14                                                                                         ##STR28##                                                         G15                                                                                         ##STR29##                                                                     R.sup.8                                                            L1          H                                                                  L2          F                                                                  L3          Cl                                                                 L4          Br                                                                 L5          J                                                                  L6          CN                                                                 L7          NO.sub.2                                                           L8          CH.sub.3                                                           L9          C.sub.2 H.sub.5                                                    L10         n-C.sub.3 H.sub.7                                                  L11         i-C.sub.3 H.sub.7                                                  L12         n-C.sub.4 H.sub.9                                                  L13         i-C.sub.4 H.sub.9                                                  L14         s-C.sub.4 H.sub.9                                                  L15         tert.-C.sub.4 H.sub.9                                              L16         CH.sub.2 F                                                         L17         CH.sub.2 Cl                                                        L18         CH.sub.2 Br                                                        L19         CHF.sub.2                                                          L20         CF.sub.3                                                           L21         CCl.sub.3                                                          L22         CH.sub.2CH.sub.2 F                                                 L23         CH.sub.2CH.sub.2 Cl                                                L24         CH.sub.2CHF.sub.2                                                  L25         CH.sub.2CF.sub.3                                                   L26         CH.sub.2CCl.sub.3                                                  L27         CF.sub.2CF.sub.3                                                   L28         CH.sub.2OCH.sub.3                                                  L29         CH.sub.2CH.sub.2OCH.sub.3                                          L30         CH(CH.sub.3)OCH.sub.3                                              L31         CH(CH.sub.3)CH.sub.2 OCH.sub.3                                     L32         CH.sub.2 OC.sub.2 H.sub.5                                          L33         CH.sub.2 C.sub.6 H.sub.5                                           L34         cyclo-C.sub.3 H.sub.5                                              L35         cyclo-C.sub.4 H.sub.7                                              L36         cyclo-C.sub.5 H.sub.9                                              L37         cyclo-C.sub.6 H.sub.11                                             L38         Tetrahydropyran-2-yl                                               L39         Tetrahydropyran-3-yl                                               L40         Tetrahydrofuran-2-yl                                               L41         Tetrahydrofuran-3-yl                                               L42         Thien-2-yl                                                         L43         Thien-3-yl                                                         L44         Furan-2-yl                                                         L45         Furan-3-yl                                                         L46         1-Methylpyrazol-3-yl                                               L47         1-Methylpyrazol-4-yl                                               L48         1-Methylpyrazol-5-yl                                               L49         1-Ethylpyrazol-3-yl                                                L50         1-Ethylpyrazol-4-yl                                                L51         1-Ethylpyrazol-5-yl                                                L52         OCH.sub.3                                                          L53         OC.sub.2 H.sub.5                                                   L54         OCH(CH.sub.3).sub.2                                                L55         OCH.sub.2 CH.sub.2 Cl                                              L56         OCH.sub.2 CH.sub.2 OCH.sub.3                                       L57         OCF.sub.3                                                          L58         OCHF.sub.2                                                         L59         OCH.sub.2 CF.sub.3                                                 L60         OC.sub.6 H.sub.5                                                   L61         OCH.sub.2 C.sub.6 H.sub.5                                          L62         SCH.sub.3                                                          L63         SCH.sub.2 CH.sub.3                                                 L64         SC.sub.6 H.sub.5                                                   L65         SCH.sub.2 C.sub.6 H.sub.5                                          L66         CH.sub.2CHCH.sub.2                                                 L67         CH(CH.sub.3)CHCH.sub.2                                             L68         CH.sub.2C(CH.sub.3) CH.sub.2                                       L69         CH.sub.2CHCHCH.sub.3                                               L70         CH.sub.2CCH                                                        L71         CH(CH.sub.3)CCH                                                    L72         CH.sub.2CCCH.sub.3                                                 L73         C.sub.6 H.sub.5                                                    L74         2-CH.sub.3C.sub.6 H.sub.4                                          L75         3-CH.sub.3C.sub.6 H.sub.4                                          L76         4-CH.sub.3C.sub.6 H.sub.4                                          L77         2-CF.sub.3C.sub.6 H.sub.4                                          L78         3-CF.sub.3C.sub.6 H.sub.4                                          L79         4-CF.sub.3C.sub.6 H.sub.4                                          L80         2-FC.sub.6 H.sub.4                                                 L81         3-FC.sub.6 H.sub.4                                                 L82         4-FC.sub.6 H.sub.4                                                 L83         2-ClC.sub.6 H.sub.4                                                L84         3-ClC.sub.6 H.sub.4                                                L85         4-ClC.sub.6 H.sub.4                                                L86         2-NO.sub.2C.sub.6 H.sub.4                                          L87         3-NO.sub.2C.sub.6 H.sub.4                                          L88         4-NO.sub.2C.sub.6 H.sub.4                                          L89         2-CH.sub.3C.sub.6 H.sub.4                                          L90         3-CH.sub.3 OC.sub.6 H.sub.4                                        L91         4-CH.sub.3 OC.sub.6 H.sub.4                                        L92         COCH.sub.3                                                         L93         COCH.sub.2 CH.sub.3                                                L94         CO(cycloC.sub.3 H.sub.5)                                           L95         COCH.sub.2 Cl                                                      L96         COCH.sub.2 Br                                                      L97         COCH.sub.2 F                                                       L98         COCF.sub.3                                                         L99         COCH.sub.2 OCH.sub.3                                               L100        CO.sub.2 H                                                         L101        CO.sub.2 CH.sub.3                                                  L102        CO.sub.2 CH.sub.2 CH.sub.3                                         L103        CO.sub.2 CH(CH.sub.3).sub.2                                        L104        CO.sub.2 CH.sub.2 CF.sub.3                                         L105        CO.sub.2 CH.sub.2 CH.sub.2 OCH.sub.3                               L106        CO.sub.2 CH.sub.2 C.sub.6 H.sub.5                                  L107        CONH.sub.2                                                         L108        CONHCH.sub.3                                                       L109        CON(CH.sub.3).sub.2                                                L110        CONHC.sub.2 H.sub.5                                                L111        CON(C.sub.2 H.sub.5).sub.2                                         L112        CONHCH(CH.sub.3).sub.2                                             L113        CONHCH.sub.2 C.sub.6 H.sub.5                                       L114        CONHC.sub.6 H.sub.5                                                L115        CONHOCH.sub.3                                                      L116        CONHOC.sub.2 H.sub.5                                               L117        SO.sub.2 N(CH.sub.3).sub.2                                         L118        SO.sub.2 NCH.sub.3 (C.sub.2 H.sub.5)                               L119        SO.sub.2 N(C.sub.2 H.sub.5).sub.2                                  L120        SO.sub.2 NHCH.sub.3                                                L121        SO.sub.2 NHC.sub.2 H.sub.5                                         L122        SO.sub.2 OCH.sub.3                                                 L123        SO.sub.2 OC.sub.2 H.sub.5                                          L124        SO.sub.2 OCH(CH.sub.3).sub.2                                       L125        SO.sub.2 OCH.sub.2 CH.sub.2 Cl                                     L126        SO.sub.2 OCH.sub.2 CF.sub.3                                        L127        OSO.sub.2 CH.sub.3                                                 L128        OSO.sub.2 C.sub.2 H.sub.5                                          L129        OSO.sub.2 CH(CH.sub.3).sub.2                                       L130        OSO.sub.2 N(CH.sub.3).sub.2                                        L131        SOCH.sub.3                                                         L132        SOC.sub.2 H.sub.5                                                  L133        SOCH(CH.sub.3).sub.2                                               L134        SOC.sub.6 H.sub.5                                                  L135        SO.sub.2 CH.sub.3                                                  L136        SO.sub.2 CH.sub.2 CH.sub.3                                         L137        SO.sub.2 CH(CH.sub.3).sub.2                                        L138        SO.sub.2 CH.sub.2 CH.sub.2 CH.sub.3                                L139        two vicinal R.sup.8 radicals                                                   together form a trimethylene chain                                 L140        two vicinal R.sup.8 radicals                                                   together form a tetramethylene chain                                           R.sup.9                                                            V1          H                                                                  V2          CH.sub.3                                                           V3          CH.sub.2 CH.sub.3                                                  V4          CH.sub.2 CH.sub.2 F                                                V5          CH.sub.2 CF.sub.3                                                  V6          CH.sub.2 CH.sub.2 Cl                                               V7          CH.sub.2 CH.sub.2 OCH.sub.3                                        V8          CH.sub.2 C.sub.6 H.sub.5                                           V9          CH(CH.sub.3).sub.2                                                 V10         cyclo-C.sub.3 H.sub.5                                              V11         cyclo-C.sub.4 H.sub.7                                              V12         cyclo-C.sub.5 H.sub.9                                              V13         C.sub.6 H.sub.5                                                    V14         2-CH.sub.3C.sub.6 H.sub.4                                          V15         2-C.sub.2 H.sub.5C.sub.6 H.sub.4                                   V16         2,6-(CH.sub.3).sub.2C.sub.6 H.sub.3                                V17         2,6-(C.sub.2 H.sub.5).sub.2C.sub.6 H.sub.3                         V18         2-CH.sub.3 -6-C.sub.2 H.sub.5C.sub.6 H.sub.3                       V19         2-ClC.sub.6 H.sub.4                                                V20         2,4-Cl.sub.2C.sub.6 H.sub.3                                        V21         2,6-Cl.sub.2C.sub.6 H.sub.3                                        V22         2,4,6-Cl.sub.3C.sub.6 H.sub.2                                      V23         2,6-Cl.sub. 2 -4-CF.sub.3C.sub.6 H.sub.2                           V24         2-Cl-4-CF.sub.3C.sub.6 H.sub.3                                     V25         CH.sub.2CHCH.sub.2                                                 V26         CHCH.sub.2                                                         V27         CH.sub.2CCH                                                        V28         CH.sub.2 C.sub.6 H.sub.5                                           V29         COCH.sub.3                                                         V30         COC.sub.2 H.sub.5                                                  V31         COC.sub.6 H.sub.5                                                  V32         CH.sub.2 F                                                         V33         CHF.sub.2                                                          V34         CF.sub.3                                                           V35         CF.sub.2 Cl                                                                    R.sup.10                                                           Y1          C.sub.6 H.sub.5                                                    Y2          2-ClC.sub.6 H.sub.4                                                Y3          2-FC.sub.6 H.sub.4                                                 Y4          2-CH.sub.3C.sub.6 H.sub.3                                          Y5          2-CF.sub.3C.sub.6 H.sub.3                                          Y6          2-OCH.sub.3C.sub.6 H.sub.3                                         Y7          2,3-Cl.sub.2C.sub.6 H.sub.3                                        Y8          2,4-Cl.sub.2C.sub.6 H.sub.3                                        Y9          2,5-Cl.sub.2C.sub.6 H.sub.3                                        Y10         2,6-Cl.sub.2C.sub.6 H.sub.3                                        Y11         2,4,6-Cl.sub.3C.sub.6 H.sub.2                                      Y12         CH.sub.2 C.sub.6 H.sub.5                                           Y13         OC.sub.6 H.sub.5                                                   Y14         OCH.sub.2 C.sub.6 H.sub.5                                          Y15         SC.sub.6 H.sub.5                                                   Y16         SCH.sub.2 C.sub.6 H.sub.5                                                      R.sup.11                                                           Z1          H                                                                  Z2          C.sub.6 H.sub.5                                                    Z3          2-ClC.sub.6 H.sub.4                                                Z4          2-FC.sub. 6 H.sub.4                                                Z5          2-CH.sub.3C.sub.6 H.sub.4                                          Z6          2-CF.sub.3C.sub.6 H.sub.4                                          Z7          2-OCH.sub.3C.sub.6 H.sub.4                                         Z8          2,4-Cl.sub.2C.sub.6 H.sub.3                                        Z9          2,6-Cl.sub.2C.sub.6 H.sub.3                                        Z10         2,6-F.sub.2C.sub.6 H.sub.3                                         Z11         2,6-(CH.sub.3).sub.2C.sub.6 H.sub.3                                Z12         2-Cl-4-CF.sub.3C.sub.6 H.sub.3                                     Z13         2,6-Cl.sub.2 -4-CF.sub.3C.sub.6 H.sub.2                            ______________________________________                                    

EXAMPLES OF USE A Herbicidal action

The herbicidal action of the sulfonamides of the formula I was demonstrated in glasshouse tests:

The plants were grown in plastic flower pots containing loamy sand with about 3% humus as substrate. The seeds of the test plants were sown separately for each species.

In the case of pre-emergence treatment, the active ingredients suspended or emulsified in water were applied directly after sowing using finely dispersing nozzles. The pots were lightly watered in order to promote germination and growth and were then covered with transparent plastic covers until the plants had started to grow. This covering results in uniform germination of the test plants unless this has been impaired by the active ingredients. The application rates were 0.125 kg/ha active substance.

For post-emergence treatment, the test plants were treated with the active ingredients suspended or emulsified in water after they had grown to a height of from 3 to 15 cm depending on species. The application rate for the post-emergence treatment was 0.25 kg/ha active substance.

The plants were kept at 10°-25° C. or 20°-35° C. depending on the species. The test period lasted 2 to 4 weeks during which time the plants were tended and their reaction to the individual treatments was evaluated.

A scale from 0 to 100 was used for evaluation. 100 means no emergence of the parts or complete destruction of, at least, the above-ground parts and zero means no damage or normal growth.

The plants used in the glasshouse tests comprised the following species:

    ______________________________________                                         Latin name           English Name                                              ______________________________________                                         Abutilon theophr.    Chinese hemp                                              Chenopodium album    white goosefoot                                           Triticum aestivum    summer wheat                                              ______________________________________                                    

When 0.25 kg/ha active substance was employed in the post-emergence procedure there is very good control with Example 40 of broad-leaved weeds while the exemplary crop wheat tolerates the treatment.

B Growth-regulating action

The growth-regulating properties of the test substances were determined by growing test plants on substrate with an adequate nutrient supply in plastic containers of diameter about 12.5 cm.

The test substances in aqueous formulations were sprayed in the post-emergence method onto the plants. The growth-regulating action was established from the measured height of growth at the end of the test. The measurements were related to the height of growth of untreated plants. 2-Chloroethyltrimethylammonium chloride was used as comparative substance A.

The reduction in longitudinal growth was accompanied by a simultaneous increase in leaf color intensity. The increased chlorophyll content suggests that the photosynthesis rate, and thus the yield, is increased.

The individual data are to be found in Tables B-1 and B-2 below.

                  TABLE B-1                                                        ______________________________________                                         Summer wheat "Ralle"; post-emergence leaf treatment                                           Concentration                                                                               Rel. growth                                        Chem. example No.                                                                             mg AS/container                                                                             height                                             ______________________________________                                         Untreated      --           100                                                A              1.5          82.2                                                              1.5          73.1                                               ______________________________________                                    

                  TABLE B-2                                                        ______________________________________                                         Summer barley "Aramir"; post-emergence leaf treatment                                         Concentration                                                                               Rel. growth                                        Chem. example No.                                                                             mg AS/container                                                                             height                                             ______________________________________                                         Untreated      --           100                                                A              1.5          90.7                                                              1.5          69.4                                               ______________________________________                                     

We claim:
 1. A sulfonamide of the formula I ##STR30## where A is ##STR31## W is oxygen or sulfur; B is 3-, 4- or 5-pyrazol disubstituted on carbon by R⁸ and monosubstituted on nitrogen by R⁹ ;R² is halogen; cyano; thiocyano; C₁ -C₆ -alkyl which is unsubstituted or substituted by at least one of the following: one to five halogens, or one of the following: C₁ -C₄ -alkoxy, C₁ -C₄ -haloalkoxy, C₁ -C₄ -alkylthio, C₁ -C₄ -haloalkylthio, phenyl, phenoxy or phenylthio, where each of the phenyls is unsubstituted or substituted by at least one of the following: one to five halogens, or one to three of the following: C₁ -C₄ -alkyl, C₁ -C₄ -haloalkyl, C₁ -C₄ -alkoxy, C₁ -C₄ -haloalkoxy, C₁ -C₄ -alkylthio or C₁ -C₄ -haloalkylthio; C₃ -C₆ -cycloalkyl, C₃ -C₈ -cycloalkoxy, C₃ -C₆ -cycloalkylthio, C₅ -C₆ -cycloalkenyl, C₅ -C₈ -cycloalkenyloxy or C₅ -C₈ -cycloalkenylthio, each of which is unsubstituted or substituted by at least one of the following: one to five halogens, or one to three of the following: C₁ -C₄ -alkyl, C₁ -C₄ -haloalkyl, C₁ -C₄ -alkoxy, C₁ -C₄ -haloalkoxy, C₁ -C₄ -alkylthio or C₁ -C₄ -haloalkylthio; phenyl, phenoxy, benzyloxy or benzylthio, each of which is unsubstituted or substituted by at least one of the following: one to five halogens, or one to three of the following: cyano, nitro, C₁ -C₄ -alkyl, C₁ -C₄ -haloalkyl, C₁ -C₄ -alkoxy, haloalkoxy, C₁ -C₄ -alkylthio or C₁ -C₄ -haloalkylthio; saturated, or unsaturated 5-7-membered heterocycle, said unsaturated 5-7 membered heterocycle having one or two double bonds, said saturated or unsaturated 5-7 membered heterocycle having one or two heteroatoms selected from nitrogen, oxygen and sulfur and which is unsubstituted or substituted by one or two of the following: halogen, cyano, nitro, C₁ -C₄ -alkyl, C₁ -C₄ -alkoxy, C₁ -C₄ -alkylthio, C₁ -C₄ -haloalkyl, C₁ -C₄ -haloalkoxy or C₁ -C₄ -haloalkylthio; C₁ -C₄ -alkoxy or C₁ -C₄ -alkylthio, C₂ -C₆ -alkenyl or C₂ -C₆ -alkenyloxy or C₂ -C₆ -alkenylthio, C₂ -C₆ -alkynyl, C₂ -C₆ -alkynyloxy or C₂ -C₆ -alkynylthio, where the said alkoxy, alkylthio, alkenyl, alkynyl, alkenyloxy(thio) and alkynyloxy(thio) is unsubstituted or substituted by at least one of the following: one to five halogens, or one of the following: C₁ -C₄ -alkoxy, C₁ -C₄ -haloalkoxy, C₁ -C₄ -alkylthio, C₁ -C₄ -haloalkylthio; phenyl, phenoxy, phenylthio, benzyloxy or benzylthio; COR¹² ; COQR¹³ ; SO₂ NR¹⁵ R¹⁶ ; SO₂ OR¹⁷ ; OSO₂ R¹⁸ ; S(O)_(n) R¹⁹ ; R³ is R⁶ ; COQR¹³ ; SO₂ NR¹⁵ R¹⁶ ; SO₂ OR¹⁷ ; OSO₂ R¹⁸ ; S(O)_(n) R¹⁹ ; R⁴ is hydrogen; halogen; cyano; C₁ -C₄ -alkyl or C₁ -C₄ -alkyl substituted by one to five halogens; C₁ -C₄ -alkoxy; C₁ -C₄ -haloalkoxy; C₁ -C₄ -alkylthio; C₁ -C₄ -haloalkylthio; R⁵ is hydrogen; nitro or R² ; R⁶ is hydrogen; halogen; cyano; C₁ -C₄ -alkyl, C₁ -C₄ -alkyl substituted by at least one of the following: one to five halogens, or one of the following: C₁ -C₄ -alkoxy, C₁ -C₄ -haloalkoxy, C₁ -C₄ -alkylthio, C₁ -C₄ -haloalkylthio, OH, SH or cyano; C₁ -C₄ -alkoxy, C₁ -C₄ -alkylthio, C₁ -C₄ -haloalkoxy or C₁ -C₄ -haloalkylthio, each of which is unsubstituted or substituted by the following: C₁ -C₄ -alkoxy, C₁ -C₄ -haloalkoxy, C₁ -C₄ -alkylthio or C₁ -C₄ -haloalkylthio; R⁸ is hydrogen; nitro; or R², or two vicinal R² together form a C₃ chain or a C₄ -C₆ chain unsubstituted or in which one methylene is replaced by oxygen or C₁ -C₄ -alkylimino; R⁹ is C₁ -C₆ -alkyl which is unsubstituted or substituted by at least one of the following: one to five halogens, or one of the following: C₁ -C₄ -alkoxy; C₁ -C₄ -haloalkoxy; C₁ -C₄ -alkylthio; C₁ -C₄ -haloalkylthio, phenyl, phenoxy or phenylthio, wherein cyclic groups are unsubstituted or substituted by at least one of the following: one to five halogens, or one to three of the following: cyano, C₁ -C₄ -alkyl, C₁ -C₄ -haloalkyl, C₁ -C₄ -alkoxy, C₁ -C₄ -haloalkoxy, C₁ -C₄ -alkylthio or C₁ -C₄ -haloalkylthio; C₃ -C₆ -cycloalkyl or C₅ -C₆ -cycloalkenyl, each of which is unsubstituted or substituted by at least one of the following: one to five halogens, or one to three of the following: C₁ -C₄ -alkyl, C₁ -C₄ -haloalkyl, C₁ -C₄ -alkoxy, C₁ -C₄ -haloalkoxy, C₁ -C₄ -alkylthio, or C₁ -C₄ -haloalkylthio; phenyl which is unsubstituted or substituted by at least one of the following: one to five halogens, or one to three of the following: cyano, nitro, C₁ -C₄ -alkyl, C₁ -C₄ -haloalkyl, C₁ -C₄ -alkoxy, C₁ -C₄ -haloalkoxy, C₁ -C₄ -alkylthio or C₁ -C₄ -haloalkylthio; C₂ -C₆ -alkenyl or C₂ -C₆ -alkynyl, each of which is unsubstituted or substituted by at least one of the following: one to five halogens, or one of the following: C₁ -C₄ -alkoxy, C₁ -C₄ -haloalkoxy, C₁ -C₄ -alkylthio or C₁ -C₄ -haloalkylthio, phenyl, phenoxy, phenylthio, benzyloxy or benzylthio; COR²¹ ; R¹⁰ is phenyl, benzyl, phenoxy, benzyloxy, phenylthio or benzylthio, each of which is unsubstituted or substituted by at least one of the following: one to five halogens, or one to three of the following: cyano, nitro, C₁ -C₄ -alkyl, C₁ -C₄ -haloalkyl, C₁ -C₄ -alkoxy, C₁ -C₄ -haloalkoxy, C₁ -C₄ -alkylthio or C₁ -C₄ -haloalkylthio; R¹¹ is hydrogen; phenyl or benzyl, each of which is unsubstituted or substituted by at least one of the following: one to five halogens, or one to three of the following: cyano, nitro, C₁ -C₄ -alkyl, C₁ -C₄ -haloalkyl, C₁ -C₄ -alkoxy, C₁ -C₄ -haloalkoxy, C₁ -C₄ -alkylthio or C₁ -C₄ -haloalkylthio; R¹² is C₁ -C₄ -alkyl which is unsubstituted or substituted by halogen or methoxy; C₃ -C₅ -cycloalkyl which is unsubstituted or substituted by chlorine or fluorine; C₃ -C₄ -alkenyl; Q is oxygen or NR¹⁴ ; R¹³ is hydrogen; C₁ -C₆ -alkyl, C₁ -C₆ -alkyl substituted by one to three of the following: halogen, C₁ -C₄ -alkoxy, C₁ -C₄ -alkylthio, C₁ -C₄ -haloalkoxy, C₁ -C₄ -alkoxy-C₁ -C₂ -alkoxy, C₃ -C₆ -cycloalkyl, or phenyl; C₃ -C₆ -cycloalkyl, which is substituted one to three times by C₁ -C₄ -alkyl; C₃ -C₆ -alkenyl; C₃ -C₆ -alkynyl; phenyl, phenyl substituted by at least one of the following: one to five halogens, or one to three of the following: cyano, nitro, C₁ -C₄ -alkyl, C₁ -C₄ -haloalkyl, C₁ -C₄ -alkoxy, C₁ -C₄ -haloalkoxy, C₁ -C₄ -alkylthio or C₁ -C₄ -haloalkylthio; R¹⁴ is OR²⁰ ; R¹³ or forms together with another R¹³ a C₄ -C₆ -alkylene chain or a C₄ -C₆ -alkylene chain in which one methylene is replaced by oxygen or C₁ -C₄ -alkylimino; R¹⁵ is C₁ -C₄ -alkyl; C₃ -C₄ -alkenyl; C₃ -C₄ -alkynyl; cyclopropylmethyl; C₃ -C₄ -cycloalkyl; R¹⁶ is hydrogen; C₁ -C₄ -alkyl; C₃ -C₄ -alkenyl; or forms together with R¹⁵ a C₄ -C₆ -alkylene chain in which one methylene can be replaced by oxygen; R¹⁷ is C₁ -C₄ -alkyl; C₁ -C₄ -haloalkyl; R¹⁸ is C₁ -C₄ -alkyl; N,N-dimethylamino; R¹⁹ is C₁ -C₄ -alkyl; C₁ -C₄ -haloalkyl; C₂ -C₄ -alkoxyalkyl; C₃ -C₄ -alkenyl; C₃ -C₄ -alkynyl; C₃ -C₄ -haloalkenyl; phenyl; phenyl substituted by fluorine, chlorine, bromine, methyl or methoxy; n is 1 or 2; R²⁰ is hydrogen or C₁ -C₄ -alkyl; R²¹ is R¹² ; phenyl or benzyl, each of which is unsubstituted or substituted by at least one of the following: one to five halogens, or one to three of the following: cyano, nitro, C₁ -C₄ -alkyl, C₁ -C₄ -haloalkyl, C₁ -C₄ -alkoxy, C₁ -C₄ -haloalkoxy, C₁ -C₄ -alkylthio or C₁ -C₄ -haloalkylthio;and the environmentally compatible salts thereof.
 2. A compound of the formula I as claimed in claim 1 or the environmentally compatible salts thereof, whereA is (A1) or (A9), W is oxygen and R⁴ is hydrogen.
 3. A compound of the formula I as claimed in claim 1 or the environmentally compatible salts thereof, whereA is (A1) or (A9), W is oxygen and R⁴ is hydrogen.
 4. A herbicide containing an effective amount of a sulfonamide of the formula I as claimed in claim 1 or the salt thereof in addition to conventional herbicidal carriers.
 5. A herbicide containing an effective amount of a sulfonamide of the formula I as claimed in claim 1, whereA is a radical of the formula (A1), W is oxygen, and R⁴ is hydrogen,or a salt thereof, and conventional herbicidal carriers.
 6. An agent for influencing plant growth, containing an effective amount of a sulfonamide of the formula I as claimed in claim 1 or the salt thereof in addition to conventional inert additives.
 7. A process for controlling undesired plant growth, which comprises allowing a sulfonamide of the formula I: ##STR32## where A is ##STR33## W is oxygen or sulfur; B is 3-, 4- or 5-pyrazolyl, disubstituted on carbon by R⁸ and monosubstituted on nitrogen by R⁹ ;R² is halogen; cyano; thiocyano; C₁ -C₆ -alkyl which is unsubstituted or substituted by at least one of the following: one to five halogens, or one of the following: C₁ -C₄ -alkoxy, C₁ -C₄ -haloalkoxy, C₁ -C₄ -alkylthio, C₁ -C₄ -haloalkylthio, phenyl, phenoxy or phenylthio, where each of the phenyls is unsubstituted or substituted by at least one of the following: one to five halogens, or one to three of the following: C₁ -C₄ -alkyl, C₁ -C₄ -haloalkyl, C₁ -C₄ -alkoxy, C₁ -C₄ -haloalkoxy, C₁ -C₄ -alkylthio or C₁ -C₄ -haloalkylthio; C₃ -C₆ -cycloalkyl, C₃ -C₈ -cycloalkoxy, C₃ -C₆ -cycloalkylthio, C₅ -C₆ -cycloalkenyl, C₅ -C₈ -cycloalkenyloxy or C₅ -C₈ -cycloalkenylthio, each of which is unsubstituted or substituted by at least one of the following: one to five halogens, or one to three of the following: C₁ -C₄ -alkyl, C₁ -C₄ -haloalkyl, C₁ -C₄ -alkoxy, C₁ -C₄ -haloalkoxy, C₁ -C₄ -alkylthio or C₁ -C₄ -haloalkylthio; phenyl, phenoxy, benzyloxy or benzylthio, each of which is unsubstituted or substituted by at least one of the following: one to five halogens, or one to three of the following: cyano, nitro, C₁ -C₄ -alkyl, C₁ -C₄ -haloalkyl, C₁ -C₄ -alkoxy, haloalkoxy, C₁ -C₄ -alkylthio or C₁ -C₄ -haloalkylthio; saturated, or unsaturated 5-7-membered heterocycle, said unsaturated 5-7 membered heterocycle having one or two double bonds, said saturated or unsaturated 5-7 membered heterocycle having one or two heteroatoms selected from nitrogen, oxygen and sulfur and which is unsubstituted or substituted by one or two of the following: halogen, cyano, nitro, C₁ -C₄ -alkyl, C₁ -C₄ -alkoxy, C₁ -C₄ -alkylthio, C₁ -C₄ -haloalkyl, C₁ -C₄ -haloalkoxy or C₁ -C₄ -haloalkylthio; C₁ -C₄ -alkoxy or C₁ -C₄ -alkylthio, C₂ -C₆ -alkenyl or C₂ -C₆ -alkenyloxy or C₂ -C₆ -alkenylthio, C₂ -C₆ -alkynyl, C₂ -C₆ -alkynyloxy or C₂ -C₆ -alkynylthio, where the said alkoxy, alkylthio, alkenyl, alkynyl, alkenyloxy(thio) and alkynyloxy(thio) is unsubstituted or substituted by at least one of the following: one to five halogens, or one of the following: C₁ -C₄ -alkoxy, C₁ -C₄ -haloalkoxy, C₁ -C₄ -alkylthio, C₁ -C₄ -haloalkylthio; phenyl, phenoxy, phenylthio, benzyloxy or benzylthio; COR¹² ; COQR¹³ ; SO₂ NR¹⁵ R¹⁶ ; SO₂ OR¹⁷ ; OSO₂ R¹⁸ ; S(O)_(n) R¹⁹ ; R³ is R⁶ ; COQR¹³ ; SO₂ NR¹⁵ R¹⁶ ; SO₂ OR¹⁷ ; OSO₂ R¹⁸ ; S(O)_(n) R¹⁹ ; R⁴ is hydrogen; halogen; cyano; C₁ -C₄ -alkyl or C₁ -C₄ -alkyl substituted by one to five halogens; C₁ -C₄ -alkoxy; C₁ -C₄ -haloalkoxy; C₁ -C₄ -alkylthio; C₁ -C₄ -haloalkylthio; R⁵ is hydrogen; nitro or R² ; R⁶ is hydrogen; halogen; cyano; C₁ -C₄ -alkyl, C₁ -C₄ -alkyl substituted by at least one of the following: one to five halogens, or one of the following: C₁ -C₄ -alkoxy, C₁ -C₄ -haloalkoxy, C₁ -C₄ -alkylthio, C₁ -C₄ -haloalkylthio, OH, SH or cyano; C₁ -C₄ -alkoxy, C₁ -C₄ -alkylthio, C₁ -C₄ -haloalkoxy or C₁ -C₄ -haloalkylthio, each of which is unsubstituted or substituted by the following: C₁ -C₄ -alkoxy, C₁ -C₄ -haloalkoxy, C₁ -C₄ -alkylthio or C₁ -C₄ -haloalkylthio; R⁸ is hydrogen; nitro; or R², or two vicinal R² together form a C₃ chain or a C₄ -C₆ chain unsubstituted or in which one methylene is replaced by oxygen or C₁ -C₄ -alkylimino; R⁹ is hydrogen; C₁ -C₆ -alkyl which is unsubstituted or substituted by at least one of the following: one to five halogens, or one of the following: C₁ -C₄ -alkoxy; C₁ -C₄ -haloalkoxy; C₁ -C₄ -alkylthio; C₁ -C₄ -haloalkylthio, phenyl, phenoxy or phenylthio, wherein cyclic groups are unsubstituted or substituted by at least one of the following: one to five halogens, or one to three of the following: cyano, C₁ -C₄ -alkyl, C₁ -C₄ -haloalkyl, C₁ -C₄ -alkoxy, C₁ -C₄ -haloalkoxy, C₁ -C₄ -alkylthio or C₁ -C₄ -haloalkylthio; C₃ -C₆ -cycloalkyl or C₅ -C₆ -cycloalkenyl, each of which is unsubstituted or substituted by at least one of the following: one to five halogens, or one to three of the following: C₁ -C₄ -alkyl, C₁ -C₄ -haloalkyl, C₁ -C₄ -alkoxy, C₁ -C₄ -haloalkoxy, C₁ -C₄ -alkylthio, or C₁ -C₄ -haloalkylthio; phenyl which is unsubstituted or substituted by at least one of the following: one to five halogens, or one to three of the following: cyano, nitro, C₁ -C₄ -alkyl, C₁ -C₄ -haloalkyl, C₁ -C₄ -alkoxy, C₁ -C₄ -haloalkoxy, C₁ -C₄ -alkylthio or C₁ -C₄ -haloalkylthio; C₂ -C₆ -alkenyl or C₂ -C₆ -alkynyl, each of which is unsubstituted or substituted by at least one of the following: one to five halogens, or one of the following: C₁ -C₄ -alkoxy, C₁ -C₄ -haloalkoxy, C₁ -C₄ -alkylthio or C₁ -C₄ -haloalkylthio, phenyl, phenoxy, phenylthio, benzyloxy or benzylthio; COR²¹ ; R¹⁰ is phenyl, benzyl, phenoxy, benzyloxy, phenylthio or benzylthio, each of which is unsubstituted or substituted by at least one of the following: one to five halogens, or one to three of the following: cyano, nitro, C₁ -C₄ -alkyl, C₁ -C₄ -haloalkyl, C₁ -C₄ -alkoxy, C₁ -C₄ -haloalkoxy, C₁ -C₄ -alkylthio or C₁ -C₄ -haloalkylthio; R¹¹ is hydrogen; phenyl or benzyl, each of which is unsubstituted or substituted by at least one of the following: one to five halogens, or one to three of the following: cyano, nitro, C₁ -C₄ -alkyl, C₁ -C₄ -haloalkyl, C₁ -C₄ -alkoxy, C₁ -C₄ -haloalkoxy, C₁ -C₄ -alkylthio or C₁ -C₄ -haloalkylthio; R¹² is C₁ -C₄ -alkyl which is unsubstituted or substituted by halogen or methoxy; C₃ -C₅ -cycloalkyl which is unsubstituted or substituted by chlorine or fluorine; C₃ -C₄ -alkenyl; Q is oxygen or NR¹⁴ ; R¹³ is hydrogen; C₁ -C₆ -alkyl, C₁ -C₆ -alkyl substituted by one to three of the following: halogen, C₁ -C₄ -alkoxy, C₁ -C₄ -alkylthio, C₁ -C₄ -haloalkoxy, C₁ -C₄ -alkoxy-C₁ -C₂ -alkoxy, C₃ -C₆ -cycloalkyl, or phenyl; C₃ -C₆ -cycloalkyl, which is substituted one to three times by C₁ -C₄ -alkyl; C₃ -C₆ -alkenyl; C₃ -C₆ -alkynyl; phenyl, phenyl substituted by at least one of the following: one to five halogens, or one to three of the following: cyano, nitro, C₁ -C₄ -alkyl, C₁ -C₄ -haloalkyl, C₁ -C₄ -alkoxy, C₁ -C₄ -haloalkoxy, C₁ -C₄ -alkylthio or C₁ -C₄ -haloalkylthio; R¹⁴ is OR²⁰ ; R¹³ or forms together with another R¹³ a C₄ -C₆ -alkylene chain or a C₄ -C₆ -alkylene chain in which one methylene is replaced by oxygen or C₁ -C₄ -alkylimino; R¹⁵ is C₁ -C₄ -alkyl; C₃ -C₄ -alkenyl; C₃ -C₄ -alkynyl; cyclopropylmethyl; C₃ -C₄ -cycloalkyl; R¹⁶ is hydrogen; C₁ -C₄ -alkyl; C₃ -C₄ -alkenyl; or forms together with R¹⁵ a C₄ -C₆ -alkylene chain in which one methylene can be replaced by oxygen; R¹⁷ is C₁ -C₄ -alkyl; C₁ -C₄ -haloalkyl; R¹⁸ is C₁ -C₄ -alkyl; N,N-dimethylamino; R¹⁹ is C₁ -C₄ -alkyl; C₁ -C₄ -haloalkyl; C₂ -C₄ -alkoxyalkyl; C₃ -C₄ -alkenyl; C₃ -C₄ -alkynyl; C₃ -C₄ -haloalkenyl; phenyl; phenyl substituted by fluorine, chlorine, bromine, methyl or methoxy; n is 1 or 2; R²⁰ is hydrogen or C₁ -C₄ -alkyl; R²¹ is R¹² ; phenyl or benzyl, each of which is unsubstituted or substituted by at least one of the following: one to five halogens, or one to three of the following: cyano, nitro, C₁ -C₄ -alkyl, C₁ -C₄ -haloalkyl, C₁ -C₄ -alkoxy, C₁ -C₄ -haloalkoxy, C₁ -C₄ -alkylthio or C₁ -C₄ -haloalkylthio; or the salt thereof to act on plants or their habitat.
 8. A process for influencing plant growth, which comprises allowing a sulfonamide of the formula I: ##STR34## where A is ##STR35## W is oxygen or sulfur; B is 3-, 4- or 5-pyrazolyl, disubstituted on carbon by R⁸ and monosubstituted on nitrogen by R⁹ ;R² is halogen; cyano; thiocyano; C₁ -C₆ -alkyl which is unsubstituted or substituted by at least one of the following: one to five halogens, or one of the following: C₁ -C₄ -alkoxy, C₁ -C₄ -haloalkoxy, C₁ -C₄ -alkylthio, C₁ -C₄ -haloalkylthio, phenyl, phenoxy or phenylthio, where each of the phenyls is unsubstituted or substituted by at least one of the following: one to five halogens, or one to three of the following: C₁ -C₄ -alkyl, C₁ -C₄ -haloalkyl, C₁ -C₄ -alkoxy, C₁ -C₄ -haloalkoxy, C₁ -C₄ -alkylthio or C₁ -C₄ -haloalkylthio; C₃ -C₆ -cycloalkyl, C₃ -C₈ -cycloalkoxy, C₃ -C₆ -cycloalkylthio, C₅ -C₆ -cycloalkenyl, C₅ -C₈ -cycloalkenyloxy or C₅ -C₈ -cycloalkenylthio, each of which is unsubstituted or substituted by at least one of the following: one to five halogens, or one to three of the following: C₁ -C₄ -alkyl, C₁ -C₄ -haloalkyl, C₁ -C₄ -alkoxy, C₁ -C₄ -haloalkoxy, C₁ -C₄ -alkylthio or C₁ -C₄ -haloalkylthio; phenyl, phenoxy, benzyloxy or benzylthio, each of which is unsubstituted or substituted by at least one of the following: one to five halogens, or one to three of the following: cyano, nitro, C₁ -C₄ -alkyl, C₁ -C₄ -haloalkyl, C₁ -C₄ -alkoxy, haloalkoxy, C₁ -C₄ -alkylthio or C₁ -C₄ -haloalkylthio; saturated, or unsaturated 5-7-membered heterocycle, said unsaturated 5-7 membered heterocycle having one or two double bonds, said saturated or unsaturated 5-7 membered heterocycle having one or two heteroatoms selected from nitrogen, oxygen and sulfur and which is unsubstituted or substituted by one or two of the following: halogen, cyano, nitro, C₁ -C₄ -alkyl, C₁ -C₄ -alkoxy, C₁ -C₄ -alkylthio, C₁ -C₄ -haloalkyl, C₁ -C₄ -haloalkoxy or C₁ -C₄ -haloalkylthio; C₁ -C₄ -alkoxy or C₁ -C₄ -alkylthio, C₂ -C₆ -alkenyl or C₂ -C₆ -alkenyloxy or C₂ -C₆ -alkenylthio, C₂ -C₆ -alkynyl, C₂ -C₆ -alkynyloxy or C₂ -C₆ -alkynylthio, where the said alkoxy, alkylthio, alkenyl, alkynyl, alkenyloxy(thio) and alkynyloxy(thio) is unsubstituted or substituted by at least one of the following: one to five halogens, or one of the following: C₁ -C₄ -alkoxy, C₁ -C₄ -haloalkoxy, C₁ -C₄ -alkylthio, C₁ -C₄ -haloalkylthio; phenyl, phenoxy, phenylthio, benzyloxy or benzylthio; COR¹² ; COQR¹³ ; SO₂ NR¹⁵ R¹⁶ ; SO₂ OR¹⁷ ; OSO₂ R¹⁸ ; S(O)_(n) R¹⁹ ; R³ is R⁶ ; COQR¹³ ; SO₂ NR¹⁵ R¹⁶ ; SO₂ OR¹⁷ ; OSO₂ R¹⁸ ; S(O)_(n) R¹⁹ ; R⁴ is hydrogen; halogen; cyano; C₁ -C₄ -alkyl or C₁ -C₄ -alkyl substituted by one to five halogens; C₁ -C₄ -alkoxy; C₁ -C₄ -haloalkoxy; C₁ -C₄ -alkylthio; C₁ -C₄ -haloalkylthio; R⁵ is hydrogen; nitro or R² ; R⁶ is hydrogen; halogen; cyano; C₁ -C₄ -alkyl, C₁ -C₄ -alkyl substituted by at least one of the following: one to five halogens, or one of the following: C₁ -C₄ -alkoxy, C₁ -C₄ -haloalkoxy, C₁ -C₄ -alkylthio, C₁ -C₄ -haloalkylthio, OH, SH or cyano; C₁ -C₄ -alkoxy, C₁ -C₄ -alkylthio, C₁ -C₄ -haloalkoxy or C₁ -C₄ -haloalkylthio, each of which is unsubstituted or substituted by the following: C₁ -C₄ -alkoxy, C₁ -C₄ -haloalkoxy, C₁ -C₄ -alkylthio or C₁ -C₄ -haloalkylthio; R⁸ is hydrogen; nitro; or R², or two vicinal R² together form a C₃ chain or a C₄ -C₆ chain unsubstituted or in which one methylene is replaced by oxygen or C₁ -C₄ -alkylimino; R⁹ is hydrogen; C₁ -C₆ -alkyl which is unsubstituted or substituted by at least one of the following: one to five halogens, or one of the following: C₁ -C₄ -alkoxy; C₁ -C₄ -haloalkoxy; C₁ -C₄ -alkylthio; C₁ -C₄ -haloalkylthio, phenyl, phenoxy or phenylthio, wherein cyclic groups are unsubstituted or substituted by at least one of the following: one to five halogens, or one to three of the following: cyano, C₁ -C₄ -alkyl, C₁ -C₄ -haloalkyl, C₁ -C₄ -alkoxy, C₁ -C₄ -haloalkoxy, C₁ -C₄ -alkylthio or C₁ -C₄ -haloalkylthio; C₃ -C₆ -cycloalkyl or C₅ -C₆ -cycloalkenyl, each of which is unsubstituted or substituted by at least one of the following: one to five halogens, or one to three of the following: C₁ -C₄ -alkyl, C₁ -C₄ -haloalkyl, C₁ -C₄ -alkoxy, C₁ -C₄ -haloalkoxy, C₁ -C₄ -alkylthio, or C₁ -C₄ -haloalkylthio; phenyl which is unsubstituted or substituted by at least one of the following: one to five halogens, or one to three of the following: cyano, nitro, C₁ -C₄ -alkyl, C₁ -C₄ -haloalkyl, C₁ -C₄ -alkoxy, C₁ -C₄ -haloalkoxy, C₁ -C₄ -alkylthio or C₁ -C₄ -haloalkylthio; C₂ -C₆ -alkenyl or C₂ -C₆ -alkynyl, each of which is unsubstituted or substituted by at least one of the following: one to five halogens, or one of the following: C₁ -C₄ -alkoxy, C₁ -C₄ -haloalkoxy, C₁ -C₄ -alkylthio or C₁ -C₄ -haloalkylthio, phenyl, phenoxy, phenylthio, benzyloxy or benzylthio; COR²¹ ; R¹⁰ is phenyl, benzyl, phenoxy, benzyloxy, phenylthio or benzylthio, each of which is unsubstituted or substituted by at least one of the following: one to five halogens, or one to three of the following: cyano, nitro, C₁ -C₄ -alkyl, C₁ -C₄ -haloalkyl, C₁ -C₄ -alkoxy, C₁ -C₄ -haloalkoxy, C₁ -C₄ -alkylthio or C₁ -C₄ -haloalkylthio; R¹¹ is hydrogen; phenyl or benzyl, each of which is unsubstituted or substituted by at least one of the following: one to five halogens, or one to three of the following: cyano, nitro, C₁ -C₄ -alkyl, C₁ -C₄ -haloalkyl, C₁ -C₄ -alkoxy, C₁ -C₄ -haloalkoxy, C₁ -C₄ -alkylthio or C₁ -C₄ -haloalkylthio; R¹² is C₁ -C₄ -alkyl which is unsubstituted or substituted by halogen or methoxy; C₃ -C₅ -cycloalkyl which is unsubstituted or substituted by chlorine or fluorine; C₃ -C₄ -alkenyl; Q is oxygen or NR¹⁴ ; R¹³ is hydrogen; C₁ -C₆ -alkyl, C₁ -C₆ -alkyl substituted by one to three of the following: halogen, C₁ -C₄ -alkoxy, C₁ -C₄ -alkylthio, C₁ -C₄ -haloalkoxy, C₁ -C₄ -alkoxy-C₁ -C₂ -alkoxy, C₃ -C₆ -cycloalkyl, or phenyl; C₃ -C₆ -cycloalkyl, which is substituted one to three times by C₁ -C₄ -alkyl; C₃ -C₆ -alkenyl; C₃ -C₆ -alkynyl; phenyl, phenyl substituted by at least one of the following: one to five halogens, or one to three of the following: cyano, nitro, C₁ -C₄ -alkyl, C₁ -C₄ -haloalkyl, C₁ -C₄ -alkoxy, C₁ -C₄ -haloalkoxy, C₁ -C₄ -alkylthio or C₁ -C₄ -haloalkylthio; R¹⁴ is OR²⁰ ; R¹³ or forms together with another R¹³ a C₄ -C₆ -alkylene chain or a C₄ -C₆ -alkylene chain in which one methylene is replaced by oxygen or C₁ -C₄ -alkylimino; R¹⁵ is C₁ -C₄ -alkyl; C₃ -C₄ -alkenyl; C₃ -C₄ -alkynyl; cyclopropylmethyl; C₃ -C₄ -cycloalkyl; R¹⁶ is hydrogen; C₁ -C₄ -alkyl; C₃ -C₄ -alkenyl; or forms together with R¹⁵ a C₄ -C₆ -alkylene chain in which one methylene can be replaced by oxygen; R¹⁷ is C₁ -C₄ -alkyl; C₁ -C₄ -haloalkyl; R¹⁸ is C₁ -C₄ -alkyl; N,N-dimethylamino; R¹⁹ is C₁ -C₄ -alkyl; C₁ -C₄ -haloalkyl; C₂ -C₄ -alkoxyalkyl; C₃ -C₄ -alkenyl; C₃ -C₄ -alkynyl; C₃ -C₄ -haloalkenyl; phenyl; phenyl substituted by fluorine, chlorine, bromine, methyl or methoxy; n is 1 or 2; R²⁰ is hydrogen or C₁ -C₄ -alkyl; R²¹ is R¹² ; phenyl or benzyl, each of which is unsubstituted or substituted by at least one of the following: one to five halogens, or one to three of the following: cyano, nitro, C₁ -C₄ -alkyl, C₁ -C₄ -haloalkyl, C₁ -C₄ -alkoxy, C₁ -C₄ -haloalkoxy, C₁ -C₄ -alkylthio or C₁ -C₄ -haloalkylthio; or the salt thereof to act on plants or their habitat. 